(4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester
• CAS No.: 145587-61-7
• Molecular Formula: C₁₈H₂₄N₂O₅
• Molecular Weight: 348.399
• Mol file: 145587-61-7.mol

Synonyms:(4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Chemical Property of (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

There total 2 articles about (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl 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: 90.0%

N-(benzyloxycarbonyl)-L-valyl-L-threonine methyl ester (7352-28-5) → (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (145587-61-7)

Guidance literature:

With polyethyleneglycol-linked N-(triethylammonium-sulfonyl)carbamate; In tetrahydrofuran; 1,4-dioxane; at 85 ℃; for 3h;

DOI:10.1016/0040-4039(96)00918-5

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → (4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (145587-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / N-methylmorpholine; isobutyl chloroformate; Et₃N / CH₂Cl₂; dimethylformamide / 0.5 h / -15 - 22 °C

2: 81 percent / Burgess reagent / tetrahydrofuran / 2.5 h / 75 °C

With 4-methyl-morpholine; Burgess Reagent; triethylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Cyclization;

DOI:10.1016/S0040-4020(00)00767-5

Reference yield: 77.0%

(4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (145587-61-7) → Cbz-Val-αThr-OMe (145678-71-3)

Guidance literature:

(4S,5S)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester; With hydrogenchloride; In tetrahydrofuran; at 22 ℃; for 30h;

With potassium carbonate; In tetrahydrofuran; for 2h; pH=9.5;

DOI:10.1016/S0040-4020(00)00767-5

upstream raw materials:

N-(benzyloxycarbonyl)-L-valyl-L-threonine methyl ester

(S)-N-(benzyloxycarbonyl)valine

Downstream raw materials:

Cbz-Val-αThr-OMe

2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-oxazole-4-carboxylic acid methyl ester

(4S,5R)-2-((1S)-1-benzyloxycarbonylamino-2-methylpropyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

4-<2-(1-benzyloxycarbonylamino-2-methylpropyl)>-5-methyl-trans-oxazoline carboxylic acid