(S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester
• CAS No.: 912656-49-6
• Molecular Formula: C₂₇H₃₂N₄O₉
• Molecular Weight: 556.572
• Mol file: 912656-49-6.mol

Synonyms:(S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester

There total 3 articles about (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl 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: 84.0%

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid (890403-75-5) + 2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester (912656-68-9) → (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester (912656-49-6)

Guidance literature:

2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester; With hydrogenchloride; In 1,4-dioxane; ethyl acetate; at 20 ℃; for 1.5h;

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid; With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol061793i

Reference yield:

(S)-methyl 2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylate (203456-93-3) → (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester (912656-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 3 h / 0 °C

2.1: HCl / dioxane; ethyl acetate / 1.5 h / 20 °C

2.2: 84 percent / DIEA; bromo-tris-pyrrolidino-phosphonium hexafluorophosphate / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate;

DOI:10.1021/ol061793i

Reference yield:

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid (890403-75-5) → (S)-4-[(S)-1-(4-Benzyloxycarbonyl-oxazol-2-yl)-2-hydroxy-ethylcarbamoyl]-2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-3'-carboxylic acid tert-butyl ester (912656-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / K₂CO₃ / dimethylformamide / 12 h / 20 °C

2.1: HCl / dioxane; ethyl acetate / 1.5 h / 20 °C

2.2: 84 percent / DIEA; bromo-tris-pyrrolidino-phosphonium hexafluorophosphate / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; potassium carbonate; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol061793i

upstream raw materials:

(S)-2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylic acid

2',2'-dimethyl-4',5'-dihydro-[2,4']bioxazolyl-4,3'-dicarboxylic acid 4-benzyl ester 3'-tert-butyl ester

(S)-methyl 2-[3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]oxazole-4-carboxylate

Downstream raw materials:

2''',2'''-dimethyl-4''',5'''-dihydro-[2,4';2',4'';2'',4''']quateroxazole-4,3'''-dicarboxylic acid 4-benzyl ester 3'''-tert-butyl ester

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