[(S)-1-((S)-2-{(S)-1-[(R)-Hydroxy-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-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)-Hydroxy-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-methyl]-2-methyl-propylcarbamoyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester
• CAS No.: 342897-21-6
• Molecular Formula: C₂₅H₃₅N₅O₇
• Molecular Weight: 517.582

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 8 articles about [(S)-1-((S)-2-{(S)-1-[(R)-Hydroxy-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-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-phenyl-3H-[1,3,4]oxadiazol-2-one; compound with toluene-4-sulfonic acid → [(S)-1-((S)-2-{(S)-1-[(R)-Hydroxy-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-methyl]-2-methyl-propylcarbamoyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (342897-21-6)

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-butoxy-N-[(1S)-1-((2R)-oxiran-2-yl)-2-methylpropyl]carboxamide (250165-20-9) → [(S)-1-((S)-2-{(S)-1-[(R)-Hydroxy-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-methyl]-2-methyl-propylcarbamoyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (342897-21-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 59 percent / Li₂CO₃ / dimethylformamide / 17 h / 100 °C

2: 90 percent / 10-camphorsulfonic acid / dimethylformamide / 2 h / 20 °C

3: 8.74 g / potassium carbonate / methanol / 3 h / 20 °C

4: 73 percent / NaIO₄; RuCl₃*nH₂O / CCl₄; acetonitrile; H₂O

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

6: triethylamine / tetrahydrofuran / 15 h / 80 °C

7: ethanol / 80 °C

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

With 4-methyl-morpholine; ruthenium trichloride; sodium periodate; (1S)-10-camphorsulfonic acid; lithium carbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

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

Reference yield:

tert-butyl (4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate (342897-05-6) → [(S)-1-((S)-2-{(S)-1-[(R)-Hydroxy-(5-oxo-4-phenyl-4,5-dihydro-[1,3,4]oxadiazol-2-yl)-methyl]-2-methyl-propylcarbamoyl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (342897-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / NaIO₄; RuCl₃*nH₂O / CCl₄; acetonitrile; H₂O

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

3: triethylamine / tetrahydrofuran / 15 h / 80 °C

4: ethanol / 80 °C

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

With 4-methyl-morpholine; ruthenium trichloride; sodium periodate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; tetrachloromethane; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

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

tert-butoxy-N-[(1S)-1-((2R)-oxiran-2-yl)-2-methylpropyl]carboxamide

tert-butyl (4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-4-(methylethyl)-1,3-oxazolidine-3-carboxylate

(3S,2R)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-methylpentyl acetate

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