4-Thiazolecarboxylic acid, 2-[(2S)-1-[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenyl propyl]-2-pyrrolidinyl]-, methyl ester

Base Information

• Chemical Name: 4-Thiazolecarboxylic acid, 2-[(2S)-1-[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenyl propyl]-2-pyrrolidinyl]-, methyl ester
• CAS No.: 347191-35-9
• Molecular Formula: C23H29N3O5S
• Molecular Weight: 459.566
• Mol file: 347191-35-9.mol

Synonyms:

Chemical Property of 4-Thiazolecarboxylic acid, 2-[(2S)-1-[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenyl propyl]-2-pyrrolidinyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Thiazolecarboxylic acid, 2-[(2S)-1-[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenyl propyl]-2-pyrrolidinyl]-, methyl ester

There total 10 articles about 4-Thiazolecarboxylic acid, 2-[(2S)-1-[(2S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenyl propyl]-2-pyrrolidinyl]-, 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: 78.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (S)-2-Pyrrolidin-2-yl-thiazole-4-carboxylic acid methyl ester; compound with trifluoro-acetic acid → methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate (347191-35-9)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1246/bcsj.75.847

Reference yield:

Boc-L-Pro-H (69610-41-9,117625-90-8) → methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate (347191-35-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 758 mg / triethylamine / toluene / 0 - 20 °C

2: 51 percent / chemical manganese dioxide / molecular sieves 4 Angstroem / benzene / 2 h / Heating

3: HCl / dioxane; H₂O / 0.33 h / 20 °C

4: 2.492 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

With hydrogenchloride; manganese(IV) oxide; diethyl cyanophosphonate; triethylamine; 4 A molecular sieve; In 1,4-dioxane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1016/S0040-4020(02)00906-7

Reference yield:

(2S)-2-(1-tert-butoxycarbonylpyrrolidin-2-yl)-thiazolidine-4-carboxylic acid methyl ester (347191-31-5) → methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate (347191-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 51 percent / chemical manganese dioxide / molecular sieves 4 Angstroem / benzene / 2 h / Heating

2: HCl / dioxane; H₂O / 0.33 h / 20 °C

3: 2.492 g / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 8 h / 0 - 20 °C

With hydrogenchloride; manganese(IV) oxide; diethyl cyanophosphonate; triethylamine; 4 A molecular sieve; In 1,4-dioxane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(02)00906-7

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-Pyrrolidin-2-yl-thiazole-4-carboxylic acid methyl ester

1-(tert-butoxycarbonyl)-L-proline

Boc-L-Pro-H

Downstream raw materials:

Boc-L-aThr-L-Phe-L-Pro-Thz-OMe

Boc-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-OMe

cyclo(-(S)-Phe-(S)-Pro-(S)-Ile-(S)-aThr-(S)-Phe-(S)-Pro-Thz-)

2-(1-{2-[2-(2-{[1-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid methyl ester