2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

Base Information

• Chemical Name: 2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester
• CAS No.: 866952-26-3
• Molecular Formula: C₂₃H₂₉N₃O₇S
• Molecular Weight: 491.565
• Mol file: 866952-26-3.mol

Synonyms:2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

Chemical Property of 2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

There total 1 articles about 2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic 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: 94.0%

methyl (3R,7R,8S,8aS)-6-tert-butoxycarbonylamino-7,8-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate (866952-15-0) + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → 2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (866952-26-3)

Guidance literature:

methyl (3R,7R,8S,8aS)-6-tert-butoxycarbonylamino-7,8-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate; With lithium hydroxide; In methanol; at 20 ℃; for 408h;

methyl (2S)-2-amino-3-phenylpropanoate; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; pH=7;

DOI:10.1002/ejoc.200500156

Reference yield: 87.0%

2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (866952-26-3) → 2-[(6-amino-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester; hydrochloride

Guidance literature:

With hydrogenchloride; In methanol; diethyl ether; for 2h;

DOI:10.1002/ejoc.200500156

Reference yield:

2-[(6-tert-butoxycarbonylamino-8-hydroxy-5-oxo-2,3,8,8a-tetrahydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl)-amino]-3-phenyl-propionic acid methyl ester (866952-26-3) → C44H48N8O11S2 (866952-31-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / HCl / methanol; diethyl ether / 2 h

2: 96 percent / PyBOP; NMM / dimethylformamide / 20 °C

3: TFA / methanol / 5 h / 20 - 45 °C

4: 0.075 mmol / PyBOP; NMM / dimethylformamide / 16 h / 20 °C / pH 8

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; trifluoroacetic acid; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500156

upstream raw materials:

methyl (3R,7R,8S,8aS)-6-tert-butoxycarbonylamino-7,8-dihydroxy-5-oxohexahydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate

methyl (2S)-2-amino-3-phenylpropanoate

Downstream raw materials:

2-{[6-(2-tert-butoxycarbonylamino-acetylamino)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carbonyl]-amino}-3-phenyl-propionic acid methyl ester

C₄₄H₄₈N₈O₁₁S₂