(2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 367260-06-8
• Molecular Formula: C₃₈H₄₇N₃O₈S
• Molecular Weight: 705.872

Synonyms:(2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester

There total 7 articles about (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic 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:

m-hydroxyphenylacetic acid (621-37-4) + (2S,4R)-1-((S)-2-Amino-2-cyclohexyl-acetyl)-4-[benzenesulfonyl-(3-benzyloxy-propyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride → (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester (367260-06-8)

Guidance literature:

With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; In dichloromethane; N,N-dimethyl-formamide; at -20 - -10 ℃;

DOI:10.1021/jo011160b

Reference yield:

benzenesulfonyl chloride (98-09-9) → (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester (367260-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 59 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 5 °C

2: 4 M HCl / dioxane / 20 °C

3: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / -20 - -10 °C

4: 34 percent / ADDP; PPh₃ / CH₂Cl₂ / 48 h / 20 °C

5: 4 M HCl / dioxane / 20 °C

6: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / -20 - -10 °C

With 4-methyl-morpholine; hydrogenchloride; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

DOI:10.1021/jo011160b

Reference yield:

1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate (121148-00-3,1018667-18-9) → (2S,4R)-4-[Benzenesulfonyl-(3-benzyloxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester (367260-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 59 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 5 °C

2: 4 M HCl / dioxane / 20 °C

3: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / -20 - -10 °C

4: 34 percent / ADDP; PPh₃ / CH₂Cl₂ / 48 h / 20 °C

5: 4 M HCl / dioxane / 20 °C

6: HOOBt; EDCI; NMM / dimethylformamide; CH₂Cl₂ / -20 - -10 °C

With 4-methyl-morpholine; hydrogenchloride; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

DOI:10.1021/jo011160b

upstream raw materials:

m-hydroxyphenylacetic acid

benzenesulfonyl chloride

1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-amino-1,2-pyrrolidinedicarboxylate

4(R)-[(phenylsulfonyl)amino]-1,2(S)-pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl)-2-methyl ester

Downstream raw materials:

methyl (7R,9S,12S)-12-cyclohexyl-11,14-dioxo-6-(phenylsulfonyl)-2-oxa-6,10,13-triazatricyclo[14.3.1.1^7,10]heneicosa-1⁽²⁰⁾,16,18-triene-9-carboxylate

(2S,4R)-4-[Benzenesulfonyl-(3-hydroxy-propyl)-amino]-1-{(S)-2-cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-pyrrolidine-2-carboxylic acid methyl ester

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