(R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

Base Information

• Chemical Name: (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid
• CAS No.: 1343489-91-7
• Molecular Formula: C₂₁H₂₅N₃O₄S₂
• Molecular Weight: 447.579
• Mol file: 1343489-91-7.mol

Synonyms:(R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

Chemical Property of (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

There total 5 articles about (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid 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: 99.0%

(S)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate (1343489-69-9) + (2R)-2-methyl-L-cysteine hydrochloride → (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1343489-91-7)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 70 ℃; for 2h; aq. phosphate buffer; Inert atmosphere;

DOI:10.1021/jo201675r

Reference yield:

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide (88463-18-7,35150-06-2) → (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1343489-91-7)

Guidance literature:

Multi-step reaction with 4 steps

1: Lawessons reagent / dichloromethane / 12 h / 20 °C

2: potassium hydrogencarbonate / 1,2-dimethoxyethane / -40 - -20 °C / Inert atmosphere

3: 2,6-dimethylpyridine; trifluoroacetic anhydride / 1,2-dimethoxyethane / -40 - -20 °C / Inert atmosphere

4: sodium hydrogencarbonate / methanol / 2 h / 70 °C / aq. phosphate buffer; Inert atmosphere

With Lawessons reagent; 2,6-dimethylpyridine; sodium hydrogencarbonate; potassium hydrogencarbonate; trifluoroacetic anhydride; In methanol; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jo201675r

Reference yield:

C17H21N3O3S → (R)-2-[2-[(S)-1-(tert-butoxycarbonylamino)-2-phenylethyl]thiazol-4-yl]-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1343489-91-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-dimethylpyridine; trifluoroacetic anhydride / 1,2-dimethoxyethane / -40 - -20 °C / Inert atmosphere

2: sodium hydrogencarbonate / methanol / 2 h / 70 °C / aq. phosphate buffer; Inert atmosphere

With 2,6-dimethylpyridine; sodium hydrogencarbonate; trifluoroacetic anhydride; In methanol; 1,2-dimethoxyethane;

DOI:10.1021/jo201675r

upstream raw materials:

(S)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide

tert-butyl [(2S)-1-amino-3-phenyl-1-thioxopropan-2-yl]carbamate