*,R^*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: *,R^*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate
• CAS No.: 101249-99-4
• Molecular Formula: C₂₂H₃₁N₃O₄
• Molecular Weight: 401.506

Synonyms:*,R^*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate

Chemical Property of *,R^*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate

Chemical Property:

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Technology Process of *,R^*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate

There total 5 articles about *,R^*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate 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:

-5-amino-7-methyl-3-octenamide (104379-95-5) + N-Benzyloxycarbonyl-L-proline (1148-11-4) → *,R*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate (101249-99-4)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jm00156a012

Reference yield:

tert-butoxycarbonyl-L-leucinal (58521-45-2) → *,R*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate (101249-99-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium/hexane / 1.) THF, -80 deg C, 45 min, 2.) THF, hexane, from -80 deg C to RT, 2 h

2: 1.) borane/THF, cyclohexene, 2.) 2 N NaOH, 30percent H₂O₂ / 1.) 0.5 h, 2.) THF, MeOH, 0.5 h

3: 1.) 4-methylmorpholine, isobutylchloroformate, 2.) concd. NH₄OH / 1.) THF, 0 deg C, 5 min, 2.) THF, 0 deg C, 1 h

4: trifluoroacetic acid (TFA) / 1 h / Ambient temperature

5: 1.54 g / 1H-benzotriazol-1-ol (HOBT), Et₃N, DCC / tetrahydrofuran / 1 h / 0 °C

With tetrahydrofuran; 4-methyl-morpholine; ammonium hydroxide; sodium hydroxide; n-butyllithium; hexane; borane; dihydrogen peroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; cyclohexene; isobutyl chloroformate; In tetrahydrofuran;

DOI:10.1021/jm00156a012

Reference yield:

-1,1-dimethylethyl <5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>carbamate (101250-70-8) → *,R*-(E))>-phenylmethyl 2-<<<5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>amino>carbonyl>-1-pyrrolidinecarboxylate (101249-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid (TFA) / 1 h / Ambient temperature

2: 1.54 g / 1H-benzotriazol-1-ol (HOBT), Et₃N, DCC / tetrahydrofuran / 1 h / 0 °C

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/jm00156a012

upstream raw materials:

-5-amino-7-methyl-3-octenamide

N-Benzyloxycarbonyl-L-proline

tert-butoxycarbonyl-L-leucinal

-1,1-dimethylethyl <5-amino-1-(2-methylpropyl)-5-oxo-2-pentenyl>carbamate

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