(+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester

Base Information

• Chemical Name: (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester
• CAS No.: 1426847-83-7
• Molecular Formula: C₂₁H₂₆N₂O₆
• Molecular Weight: 402.447
• Mol file: 1426847-83-7.mol

Synonyms:(+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester

Chemical Property of (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester

There total 7 articles about (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester 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: 74.0%

(S)-benzyl 2-(1-(3,4-dimethoxyphenyl)-3-methoxy-2-methyl-1,3-dioxopropan-2-yl)hydrazinecarboxylate (1426847-82-6) → (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester (1426847-83-7)

Guidance literature:

(S)-benzyl 2-(1-(3,4-dimethoxyphenyl)-3-methoxy-2-methyl-1,3-dioxopropan-2-yl)hydrazinecarboxylate; With trifluoroacetic acid; for 0.0833333h; Inert atmosphere; Molecular sieve;

With dimethylethylsilane; for 18h; Reagent/catalyst; Time; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol400136y

Reference yield:

(+)-1-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester (1281895-44-0) → (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester (1426847-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid

2.1: sodium hydrogencarbonate / tetrahydrofuran / 0.5 h / 20 °C

3.1: trifluoroacetic acid / 0.08 h / Inert atmosphere; Molecular sieve

3.2: 18 h / Inert atmosphere; Molecular sieve

With sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ol400136y

Reference yield:

methyl 3-(3,4-dimethoxyphenyl)-2-methyl-3-oxopropanoate (168165-94-4) → (+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester (1426847-83-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: europium(III) trifluoromethanesulfonate; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine / acetonitrile / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.1: trifluoroacetic acid

3.1: sodium hydrogencarbonate / tetrahydrofuran / 0.5 h / 20 °C

4.1: trifluoroacetic acid / 0.08 h / Inert atmosphere; Molecular sieve

4.2: 18 h / Inert atmosphere; Molecular sieve

With sodium hydrogencarbonate; trifluoroacetic acid; europium(III) trifluoromethanesulfonate; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine; In tetrahydrofuran; acetonitrile; 1.1: |Michael Addition;

DOI:10.1021/ol400136y

upstream raw materials:

(+)-1-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester

(S)-benzyl 2-(1-(3,4-dimethoxyphenyl)-3-methoxy-2-methyl-1,3-dioxopropan-2-yl)hydrazinecarboxylate

1-(3,4-dimethoxyphenyl)ethanone

methyl 3-(3,4-dimethoxyphenyl)-3-oxopropionate

Downstream raw materials:

S(-)-carbidopa

Refernces

• 1、 Pericas, Lex,Shafir, Alexandr,Vallribera, Adelina. "Asymmetric Synthesis of L-carbidopa based on a highly enantioselective α-amination". . p. 1448 - 1451. Retrieved 2013/06/27.