(3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate HCl
(3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate HCl
(3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride is a stereodefined chiral building block bearing three contiguous stereocenters, making it a valuable intermediate in the asymmetric synthesis of complex bioactive molecules.
- Product SKU
- T692826
- Chemical Name
- (3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride
- Stereochemistry
- Three defined stereocenters at C3 (R), C4 (S), and C5 (S)
- Functional Groups
- tert-Butyl ester, methoxy ether, secondary methylamino group (as HCl salt)
- Primary Application
- Chiral intermediate for asymmetric synthesis and pharmaceutical research
- Salt Form
- Hydrochloride salt, enhancing stability and handling convenience
Chemical Identity and Structural Features
(3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride (SKU: T692826) is a stereochemically well-defined organic compound featuring three contiguous chiral centers located at the C3, C4, and C5 positions of its heptanoate backbone. The absolute configurations are assigned as 3R, 4S, and 5S, respectively, providing a rigid and predictable three-dimensional scaffold for downstream chemical transformations.
The molecule incorporates a tert-butyl ester moiety, which serves as a protecting group for the carboxylic acid function. This group can be selectively removed under mild acidic conditions, for example using trifluoroacetic acid (TFA), without disturbing other sensitive functionalities. A methoxy ether at C3 introduces an additional degree of polarity and a handle for further functionalization. The secondary methylamino group at C4, presented as its hydrochloride salt, is protected from unwanted reactions during storage and can be liberated with a suitable base when required for synthesis.
The hydrochloride salt form improves the compound's physicochemical stability, hygroscopicity profile, and ease of handling and weighing in a laboratory environment, which is particularly advantageous when working with sub-gram quantities.
Synthesis Relevance and Role as a Pharmaceutical Intermediate
Compounds bearing multiple contiguous stereocenters with defined absolute configurations are highly sought after as chiral building blocks in medicinal chemistry and process chemistry. The 3-methoxy-5-methyl-4-(methylamino)heptanoate scaffold found in this compound is structurally related to fragments that appear in the synthesis of complex natural products and pharmaceutical agents, particularly those targeting peptide-based or peptidomimetic drug candidates.
The combination of a protected amine (as HCl salt), a protected acid (tert-butyl ester), and a methoxy group creates a trifunctional intermediate that can be selectively deprotected and coupled in a convergent synthesis strategy. The secondary methylamino group is compatible with standard amide bond-forming reactions, reductive amination, and N-alkylation after liberation from its salt form, providing synthetic versatility.
The tert-butyl ester orthogonality with respect to benzyl- or methyl-based ester protecting groups further increases the utility of this compound in multi-step total synthesis sequences where differential protection and deprotection steps are essential.
Handling, Storage, and Safety Considerations
As with all fine chemical reagents containing amine functionalities, appropriate personal protective equipment (PPE) should be worn when handling (3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride. This includes laboratory coat, chemical-resistant gloves, and eye protection. Work should be conducted in a well-ventilated fume hood to minimize inhalation exposure to dust or aerosols.
The compound should be stored in a tightly sealed container, away from moisture and light, at the temperature specified on the product label. The hydrochloride salt form generally imparts greater stability compared to the free base under ambient conditions; however, prolonged exposure to humid environments should be avoided to prevent potential hydrolysis of the tert-butyl ester or deliquescence of the salt.
Prior to use, users should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for detailed hazard classifications, first-aid measures, and disposal procedures. Waste containing this compound should be disposed of in accordance with local and institutional chemical waste regulations.
Quality, Purity, and Ordering Information
Aladdin Scientific supplies (3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride under SKU T692826. Researchers and procurement managers are encouraged to request a Certificate of Analysis (CoA) for each lot, which typically includes data from techniques such as high-performance liquid chromatography (HPLC) for purity assessment, nuclear magnetic resonance (NMR) spectroscopy for structural confirmation, and optical rotation or chiral HPLC to verify stereochemical integrity.
For research applications where stereochemical fidelity is paramount — such as the synthesis of clinical candidates or reference standards — verification of enantiomeric and diastereomeric excess is strongly recommended prior to use. Aladdin Scientific's quality control processes aim to ensure consistent lot-to-lot reproducibility for this compound.
To place an order or inquire about custom quantities, bulk pricing, or additional analytical data, please contact Aladdin Scientific's customer service team or visit the product page for T692826 on the Aladdin Scientific website.
Frequently asked questions
What is the significance of the three stereocenters in this compound?
The three contiguous stereocenters at C3 (R), C4 (S), and C5 (S) define a unique three-dimensional shape that is critical for molecular recognition events in biological systems and for achieving the correct spatial arrangement required in a target natural product or drug molecule. Using a compound with defined absolute configuration avoids the need for costly chiral resolution steps later in a synthesis.
How should the tert-butyl ester be removed during synthesis?
The tert-butyl ester can typically be cleaved under mild acidic conditions using reagents such as trifluoroacetic acid (TFA) in dichloromethane, or hydrochloric acid in dioxane. These conditions are generally selective for tert-butyl esters and do not affect most other common protecting groups. Reaction conditions should be optimized based on the specific synthetic context to avoid undesired side reactions.
How do I verify the stereochemical integrity of the compound upon receipt?
Stereochemical integrity can be verified by measuring the optical rotation of the compound and comparing it against reference values, or by chiral HPLC analysis to determine enantiomeric and diastereomeric excess. Aladdin Scientific provides a Certificate of Analysis (CoA) per lot; customers requiring additional stereochemical data may contact our technical support team.
Can the methylamino group be used directly in amide coupling reactions?
The methylamino group is present as its hydrochloride salt and must first be liberated to the free base by treatment with a suitable base (e.g., triethylamine or diisopropylethylamine) before it can participate in amide coupling reactions. Once free, the secondary amine is reactive toward activated esters, acid chlorides, and standard coupling reagents such as HATU or EDC/HOBt.
References
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: Hoboken, NJ, 2007.
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012.
- Aladdin Scientific. Product page for T692826: (3R,4S,5S)-tert-Butyl 3-methoxy-5-methyl-4-(methylamino)heptanoate hydrochloride. Aladdin Scientific website (accessed 2024).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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