Name: (R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate
CAS No.: 880468-89-3
EINECS No.: 1592732-453-0
Chemical Formula: C₁₆H₂₄N₂O₄
Molecular Weight: 308.37 g/mol
InChI 1S/C16H24N2O4/c1-16(2,3)22-15(20)18-13(11-21-4)14(19)17-10-12-8-6-5-7-9-12/h5-9,13H,10-11H2,1-4H3,(H,17,19)(H,18,20)/t13-/m1/s1
Density 1.103±0.06 g/cm³ (Predicted)
Boiling Point 507.6±50.0 °C (Predicted)
Flash Point 260.5±30.1 °C (Predicted)
Water Solubility Slightly soluble in water; soluble in chloroform, DMSO, and ethyl acetate
Vapor Pressure 1.0±0.3 mmHg at 25°C (Predicted)
Refractive Index 1.498±0.06 (Predicted)
Storage Conditions: Store in a sealed container in a dry, cool, and well-ventilated place; store at room temperature; avoid light and moisture.
Sensitivity: Sensitive to moisture; avoid contact with strong oxidizers, strong acids, and strong alkalis.
Appearance: White to off-white crystalline powder or solid.
Specific Gravity: 1.103 (Predicted)
Color: White to Off-White
Hazard Symbols: Not hazardous; no special hazard symbols.
Risk Terms: R36/37/38 (Irritation to eyes, respiratory system, and skin)
Safety Terms: S26 (In case of accidental contact with eyes, rinse immediately with plenty of water and consult a doctor); S36 (Wear appropriate protective clothing)
Customs Code: 2924.29.90 (Organic compounds containing amide groups)
Properties: This product is a chiral compound with an (R) configuration and is a key intermediate in the synthesis of lacosamide. This compound contains functional groups such as a tert-butyloxycarbonyl (Boc) protecting group, a benzylamide group, and a methoxy group, exhibiting a stable molecular structure. It is a solid at room temperature with a melting point of approximately 63-64°C. The compound possesses a chiral center, exhibits high optical purity, and is sensitive to moisture, requiring storage under dry conditions.
Chiral Purity: Optical purity (ee value) ≥99%, ensuring the chiral quality of the downstream product lacosamide.
Stability: Stable under dry, light-protected conditions; Boc deprotection reaction can occur under acidic conditions.
Solubility: Easily soluble in organic solvents such as dichloromethane, chloroform, and ethyl acetate; slightly soluble in water.
Reactivity: The Boc group can be deprotected under acidic conditions (such as TFA and HCl) to generate a free amine intermediate.
Uses
1. Pharmaceutical Intermediate (Core Use)
This product is a key synthetic intermediate for the antiepileptic drug lacosamide (trade name: Vimpat®). Lacosamide is a novel anticonvulsant drug developed by UCB Pharma for the treatment of partial seizures and diabetic neuropathic pain. This product, as an amide intermediate in the synthetic route of lacosamide, yields the final API through Boc deprotection and acetylation.
2. Drug Impurity Reference Standard
This product can be used as an impurity reference standard (Impurity A) for the quality control of lacosamide API and its formulations, for HPLC analytical method development, impurity profile studies, and quality standard establishment.
3. Research and Synthetic Building Block
As a Boc-protected chiral aminoamide compound, it can be used in peptide synthesis, chiral catalyst ligand development, and the synthetic research of other chiral drug intermediates.
️ Preparation Method
Main Synthetic Process (Four-Step Method):
Amino Protection: Starting with D-serine, amino protection is performed under basic conditions with di-tert-butyl dicarbonate (Boc₂O) to obtain N-Boc-D-serine.
Carboxyl activation and amidation: N-Boc-D-serine undergoes a condensation reaction with benzylamine via isobutyl chloroformate (IBCF) to generate a hydroxyl intermediate.
O-methylation: Under alkaline conditions (e.g., NaOH/KOH), the hydroxyl group is methylated using dimethyl sulfate (DMS) to obtain the target product.
Purification and refining: High-purity (≥98%) product is obtained by recrystallization (ethyl acetate/n-hexane system) or column chromatography.
Process optimization directions: Using a phase transfer catalyst (TBAB) can reduce racemization; using an aqueous phase system for methylation can reduce production costs and improve safety.
️ Safety Information
Personal Protective Equipment: Wear protective eyewear, gloves, and a dust mask during handling; avoid inhaling dust.
Storage Requirements: Store in a cool, dry, and well-ventilated warehouse in a sealed container; keep away from fire and heat sources.
Compatibility: Avoid contact with strong oxidizers, strong acids, and strong alkalis; avoid humid environments.
First Aid Measures: Wash skin immediately with soap and water after contact; flush eyes with plenty of water and seek medical attention after contact.
Disposal: Dispose of in accordance with local environmental regulations; do not dump indiscriminately.
Transportation Classification: Not a hazardous material; transport as general chemicals; keep packaging intact and prevent moisture absorption.
Large-Scale Production Capacity: Annual production capacity up to 500 kg, meeting the needs of all stages from laboratory research and development to commercial production; supports ton-level order customization.
Superior Quality: Purity ≥98% (HPLC), chiral purity (ee value) ≥99.5%, single impurities controlled below 0.1%, conforming to ICH Q3A quality standards.
Comprehensive Quality Control Equipped with a full range of analytical instruments including HPLC, GC, NMR, MS, XRPD, and DSC; each batch provides a Certificate of Analysis (COA), HPLC chromatogram, and chiral analysis report.
Cost Advantage: Self-optimized synthesis process using a green chemistry route, reducing raw material costs by 20%, providing customers with highly competitive prices.
Stable Supply: 100 kg of stock is maintained; regular orders are shipped within 48 hours; global logistics delivery (air/sea/express) is supported.
Customization Services: Flexible packaging from gram to ton level is available (1g/5g/25g/100g/1kg/5kg/25kg).
Compliance Guarantee: ISO 9001 quality management system certified; complete DMF/CTD documentation provided; audit assistance available.
Post time: Jun-05-2026
