(S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide

Base Information

• Chemical Name: (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide
• CAS No.: 136138-87-9
• Molecular Formula: C₃₇H₅₁N₇O₈S
• Molecular Weight: 753.92

Synonyms:

Chemical Property of (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide

Chemical Property:

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Useful:

Technology Process of (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide

There total 4 articles about (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide 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: 38.7%

(S)-2-{2-[(S)-2-((S)-3-Amino-2-hydroxy-4-phenyl-butyrylamino)-3-phenyl-propionylamino]-acetylamino}-4-methyl-pentanoic acid ((S)-1-carbamoyl-3-methylsulfanyl-propyl)-amide; hydrochloride (136138-80-2,136233-26-6) + L-Pyroglutamic acid (98-79-3) → (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide (136138-87-9,136314-62-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/0223-5234(91)90104-U

Reference yield:

(R,S)-α-hydroxy, (S)-β-amino, 4-phenylbutyric acid hydrochloride (1201292-56-9) → (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide (136138-87-9,136314-62-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 68.7 percent / aq. NaOH / dioxane / 1 h / 0 °C

2: 60.8 percent / 1-hydroxybenzotriazole (HOBt), N,N-dicyclohexylcarbodiimide (DCC), NMM / dimethylformamide / Ambient temperature

3: 90 percent / HCl / ethyl acetate / 1 h / Ambient temperature

4: 38.7 percent / 1-hydroxybenzotriazole (HOBt), N,N-dicyclohexylcarbodiimide (DCC), NMM / dimethylformamide / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In 1,4-dioxane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90104-U

Reference yield:

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid (191849-93-1) → (S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-benzyl-2-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-hydroxy-ethyl}-amide (136138-87-9,136314-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 60.8 percent / 1-hydroxybenzotriazole (HOBt), N,N-dicyclohexylcarbodiimide (DCC), NMM / dimethylformamide / Ambient temperature

2: 90 percent / HCl / ethyl acetate / 1 h / Ambient temperature

3: 38.7 percent / 1-hydroxybenzotriazole (HOBt), N,N-dicyclohexylcarbodiimide (DCC), NMM / dimethylformamide / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0223-5234(91)90104-U

upstream raw materials:

(S)-2-{2-[(S)-2-((S)-3-Amino-2-hydroxy-4-phenyl-butyrylamino)-3-phenyl-propionylamino]-acetylamino}-4-methyl-pentanoic acid ((S)-1-carbamoyl-3-methylsulfanyl-propyl)-amide; hydrochloride

L-Pyroglutamic acid

(R,S)-α-hydroxy, (S)-β-amino, 4-phenylbutyric acid hydrochloride

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid

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