R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid

Base Information

• Chemical Name: R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid
• CAS No.: 917252-91-6
• Molecular Formula: C₂₀H₂₈N₂O₅S
• Molecular Weight: 408.519

Synonyms:R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid

Chemical Property of R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid

Chemical Property:

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Technology Process of R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid

There total 2 articles about R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-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: 30.0%

L-(-)-2,2-dimethylthiazolidine-4-carboxylic acid hydrochloride salt (67089-92-3) + 1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate (133010-06-7) → R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid (917252-91-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 3h;

DOI:10.1016/j.tet.2006.09.009

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid (917252-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / pyridine; 2,4,6-trifluoro-1,3,5-triazine / CH₂Cl₂ / 2 h / -10 °C

2: 30 percent / ethyldiisopropylamine / dimethylformamide / 3 h

With pyridine; trifluoro-[1,3,5]triazine; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.09.009

Reference yield: 92.0%

R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylic acid (917252-91-6) + 2,3,4,5,6-pentafluorophenol (771-61-9) → pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylate (917253-02-2)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 0 ℃; for 3h;

DOI:10.1016/j.tet.2006.09.009

upstream raw materials:

L-(-)-2,2-dimethylthiazolidine-4-carboxylic acid hydrochloride salt

1,1-dimethylethyl S-N-(1-fluorocarbonyl-2-phenylethyl)carbamate

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

pentafluorophenyl R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)tetrahydrothiazole-4-carboxylate

R-2,2-dimethyl-3-(N-(1,1-dimethylethoxycarbonyl)-L-phenylalanyl)-N-(2-(4-nitrophenyl)ethyl)tetrahydrothiazole-4-carboxamide

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