(S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate

Base Information

• Chemical Name: (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate
• CAS No.: 1246370-69-3
• Molecular Formula: C₃₂H₃₁NO₆
• Molecular Weight: 525.601
• Mol file: 1246370-69-3.mol

Synonyms:(S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate

Chemical Property of (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate

There total 5 articles about (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate 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: 88.0%

benzyl bromide (100-39-0) + (S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate (37169-46-3) → (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate (1246370-69-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 1h; Cooling with ice;

Reference yield:

benzyl 4-nitrophenyl carbonate (13795-24-9) + 3-(3,4-bis-benzyloxyphenyl)-2-tert-(butoxycarbonylamino)propionic acid methyl ester (125228-11-7) → (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate (1246370-69-3)

Guidance literature:

3-(3,4-bis-benzyloxyphenyl)-2-tert-(butoxycarbonylamino)propionic acid methyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

benzyl 4-nitrophenyl carbonate; With triethylamine; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1002/anie.202100873

Reference yield:

levodopa (59-92-7,90638-38-3) → (S)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoate (1246370-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 14 h / -5 - 50 °C

2: triethylamine / N,N-dimethyl-formamide / 1.5 h / 10 - 35 °C / Cooling with ice

3: potassium carbonate / N,N-dimethyl-formamide / 1 h / 50 °C / Cooling with ice

With thionyl chloride; potassium carbonate; triethylamine; In N,N-dimethyl-formamide;

upstream raw materials:

benzyl bromide

(S)-methyl 2-(benzyloxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate

levodopa

L-dopa methyl ester hydrochloride

Downstream raw materials:

(S)-3-(3,4-bis(benzyloxy)phenyl)-2-(benzyloxycarbonylamino)propanoic acid