2-Allyl-2-[3-methyl-1-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamoyl)-butyl]-pent-4-enoic acid tert-butyl ester → 2-Allyl-2-[3-methyl-1-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-3-ylcarbamoyl)-butyl]-pent-4-enoic acid

HRID 1635108

Reaction equation

HRID 1635108 reaction equation
C([O:5][C:6](=[O:41])[C:7]([CH2:38][CH:39]=[CH2:40])([CH:11]([C:16](=[O:37])[NH:17][CH:18]1[C:24](=[O:25])[N:23]([CH3:26])[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:19]1)[CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH:9]=[CH2:10])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:8]([C:7]([CH:11]([C:16](=[O:37])[NH:17][CH:18]1[C:24](=[O:25])[N:23]([CH3:26])[C:22]2[CH:27]=[CH:28][CH:29]=[CH:30][C:21]=2[C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:19]1)[CH2:12][CH:13]([CH3:15])[CH3:14])([CH2:38][CH:39]=[CH2:40])[C:6]([OH:41])=[O:5])[CH:9]=[CH2:10]

Participants

3

Reactant 1

HCID 235552212-Allyl-2-[3-methyl-1-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylcarbamoyl)-butyl]-pent-4-enoic acid tert-butyl ester

Product 1

HCID 222882322-Allyl-2-[3-methyl-1-(1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-3-ylcarbamoyl)-butyl]-pent-4-enoic acidYield 92.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of compound 29 (300 mg, 0.54 mmol) in 50 ml TFA/CH2Cl2 (1:1) was stirred for 2 hr at ambient temperature, then concentrated under vacuum. Two cycles of toluene addition and removal of volatiles gave 250 mg of 30 as a white solid (92%) which was used in the next step without purification. ESI ES+=502.3 (M+1).

Workup

  1. concentrationconcentrated under vacuum
  2. additionTwo cycles of toluene addition and removal of volatiles

Sources & evidence

ORD record
ord-5e1099a2fc824150ac87587603896384
Source dataset
uspto-grants-2003_01
Patent number
US06509333B2

Linked notes

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