{(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

Base Information

• Chemical Name: {(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester
• CAS No.: 342897-32-9
• Molecular Formula: C₂₇H₄₀N₆O₇
• Molecular Weight: 560.651

Synonyms:

Chemical Property of {(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

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Technology Process of {(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

There total 2 articles about {(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic 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:

(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carboxylic acid (181827-47-4) + 5-((1R,2S)-2-Amino-1-hydroxy-3-methyl-butyl)-3-(4-dimethylamino-phenyl)-3H-[1,3,4]oxadiazol-2-one; compound with toluene-4-sulfonic acid → {(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (342897-32-9)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 7h;

DOI:10.1016/S0968-0896(01)00007-4

Reference yield:

tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate (342897-31-8) → {(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (342897-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 80 °C

2: N-hydroxybenzotriazole hydrate; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; N-methylmorpholine / dimethylformamide / 7 h / 20 °C

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(01)00007-4

Reference yield:

{(S)-1-[(S)-2-((S)-1-{(R)-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazol-2-yl]-hydroxy-methyl}-2-methyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester (342897-32-9) → [(S)-1-((S)-2-{(S)-1-[4-(4-Dimethylamino-phenyl)-5-oxo-4,5-dihydro-[1,3,4]oxadiazole-2-carbonyl]-2-methyl-propylcarbamoyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

Guidance literature:

With 4-methyl-morpholine; oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -70 - -20 ℃; for 2.5h;

DOI:10.1016/S0968-0896(01)00007-4

upstream raw materials:

(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carboxylic acid

tert-butyl (4S,5R)-5-{3-[4-(dimethylamino)phenyl]-2-oxo-1,3,4-oxadiazolin-5-yl}-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

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