4-Nitrophenyl chloroformate → HCID 86597452, compound

HRID 1374559Notes

Reaction equation

HRID 1374559 reaction equation
[C:1]([N:4]1[CH2:10][C@H:9]([NH:11][C:12](=[O:16])[C@@H:13]([OH:15])[CH3:14])[C:8](=[O:17])[N:7]([CH3:18])[C:6]2[CH:19]=[CH:20][CH:21]=[CH:22][C:5]1=2)(=[O:3])[CH3:2].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:25]>N1C=CC=CC=1>[N+:33]([C:30]1[CH:29]=[CH:28][C:27]([O:26][C:24](=[O:25])[O:15][C@H:13]([C:12](=[O:16])[NH:11][C@@H:9]2[C:8](=[O:17])[N:7]([CH3:18])[C:6]3[CH:19]=[CH:20][CH:21]=[CH:22][C:5]=3[N:4]([C:1](=[O:3])[CH3:2])[CH2:10]2)[CH3:14])=[CH:32][CH:31]=1)([O-:35])=[O:34]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 69507875HCID 69507875, compound

Product 1

HCID 86597452HCID 86597452, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 50 mg (0.16 mmol) of (S)—N—((S)-5-acetyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-2-hydroxy-propionamide in 1.5 ml of pyridine was treated with 39 mg (0.18 mmol) of 4-nitrophenyl chloroformate, and the mixture was stirred at room temperature for 18 h. For the working-up, the solvent was evaporated and the residue chromatographed on silica gel using a 3:1-mixture of heptane and ethyl acetate as the eluent. There were obtained 31 mg (40% of theory) of carbonic acid (S)-1-((S)-5-acetyl-1-methyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl)-ethyl ester 4-nitro-phenyl ester; MS: m/e=488 (M+NH4)+. The ester was treated with 0.7 ml of 2,2,3,3,3-pentafluoro-propylamine and the mixture was stirred at room temperature for 36 h. For the working-up, 3 ml of ethyl acetate were added and the solution was washed with a saturated solution of sodium carbonate and a saturated solution of sodium chloride. The organic layer was dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a gradient of a 98:2- to 95:5-mixture of dichloromethane and methanol as the eluent. There were obtained 12 mg (38% of theory) of the title compound as a white solid; MS: m/e=498 (M+NH4)+.

Workup

  1. customthe solvent was evaporated
  2. customthe residue chromatographed on silica gel using a 3

Sources & evidence

ORD record
ord-04f04bb21e6141548e07630195a6ee2a
Source dataset
uspto-grants-2007_01
Patent number
US07166587B2

Reaction notes

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