(R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate

Base Information

• Chemical Name: (R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate
• CAS No.: 880468-89-3
• Molecular Formula: C16H24 N2 O4
• Molecular Weight: 308.378
• Hs Code.: 2924299090
• Mol file: 880468-89-3.mol

Synonyms:TERT-BUTYL N-[(1R)-1-(BENZYLCARBAMOYL)-2-METHOXYETHYL]CARBAMATE;(R)-TERT-BUTYL-1-(BENZYLAMINO)-3-METHOXY-1-OXOPROPAN-2-YLCARBAMATE;(R)-N-benzyl-2-N-Boc-amino-3-methoxypropionamide;

Chemical Property of (R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate

Chemical Property:

• Melting Point: 63-64 °C
• Boiling Point: 507.6±50.0 °C(Predicted)
• PKA: 10.62±0.46(Predicted)
• PSA: 76.66000
• Density: 1.103±0.06 g/cm3(Predicted)
• LogP: 2.62430
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

(R)-tert-Butyl1-(Benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-tert-Butyl 1-(Benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate is an intermediate in the synthesis of functionalized amino acids, and in the synthesis of antiepileptic drug (R)-lacosamide.

Technology Process of (R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate

There total 17 articles about (R)-tert-Butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-Boc-O-methyl-D-serine pivalic anhydride + benzylamine (100-46-9) → tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate (880468-89-3)

Guidance literature:

In dichloromethane; at 0 - 5 ℃; for 0.5h;

Reference yield: 96.28%

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate (1253790-58-7) + dimethyl sulfate (77-78-1) → tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate (880468-89-3)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In water; toluene; at 0 - 30 ℃; for 1.5h;

Reference yield: 90.4%

2,4-dioxo-3-azaspiro[5.5]undecan-3-yl N-(tert-butoxycarbonyl)-O-methyl-D-serinate + benzylamine (100-46-9) → tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate (880468-89-3)

Guidance literature:

at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2016.04.007

upstream raw materials:

benzylamine

(R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid

tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate

dimethyl sulfate

Downstream raw materials:

lacosamide

(R)-2-amino-N-benzyl-3-methoxypropionamide hydrochloride

(R)-2-amino-N-benzyl-3-methoxypropanamide

Refernces

• 1、 Yang, Anjiang,Hu, Feifei,Li, Zhong,Chen, Mengdi,Cai, Jianguang,Wang, Linghui,Zhang, Tao,Zhao, Chuanmeng,Zhang, Fuli. "Improved Synthesis and Impurity Identification of (R)-Lacosamide". . p. 818 - 824. Retrieved 2019/04/01.
• 2、 -. "Improved preparation method of modified lacosamide". Paragraph 0036; 0045-0047. . Retrieved 2017/08/31.