Dimethylformamide → N-(t-butyloxycarbonyl)-4-phenacyloxy-L-phenylalanine cyclohexylamide

HRID 330434Notes

Reaction equation

HRID 330434 reaction equation
C[CH:2]1[CH:7](C)[CH2:6][CH2:5][CH:4]([NH:9][C:10](=[O:35])[C@H:11]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28]C3C=CC=CC=3)=[CH:23][CH:22]=2)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3]1.[H-].[Na+].C([C:40]1[CH:41]=[C:42]([CH:45]=[CH:46][CH:47]=1)[CH2:43]Br)#N.CN(C)C=[O:51]>>[CH:4]1([NH:9][C:10](=[O:35])[C@H:11]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:43]([C:42]3[CH:41]=[CH:40][CH:47]=[CH:46][CH:45]=3)=[O:51])=[CH:25][CH:26]=2)[NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:5][CH2:6][CH2:7][CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 54300108N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide

Product 1

HCID 70070014N-(t-butyloxycarbonyl)-4-phenacyloxy-L-phenylalanine cyclohexylamide

Procedure

N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 4-acetylanilide (1.2 g), palladium black (0.15 g) and cyclohexene (8 ml) were added into ethanol (40 ml) and the reaction was carried out under reflux of ethanol for 1 hour. After cooling, the mixture was filtered and a filtrate was concentrated under a reduced pressure to obtain N-(t-butyloxycarbonyl)-4-hydroxy-L-phenylalanine 4-acetylanilide (I) (0.99 g). The above compound (I) (0.99 g) was dissolved in dimethylformamide (30 ml), added with oily sodium hydride (0.1 g) and the mixture was stirred at room temperature for 30 minutes. A solution of 3-cyanobenzylbromide (0.4 g) in dimethylformamide (5 ml) was added and allowed to react at room temperature for 6 hours, and the reaction mixture was poured into ice-water (100 ml) and extracted with ethyl acetate. A conventional post-treatment was carried out to obtain N-(t-butyloxycarbonyl)-4-(3-cyanobenzyloxy)-L-phenylalanine 4-acetylanilide (II) (1.25 g). The above compound (II) (1.25 g) was allowed to react with 4N-hydrogen chloride/dioxane (12 ml) to obtain 4-(3-cyanobenzyloxy)-L-phenylalanine 4-acetylanilide (III).

Workup

  1. customto react at room temperature for 6 hours
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-bb1fdf93d62444ef82b4e9e8df884352
Source dataset
uspto-grants-1990_01
Patent number
US04895842

Reaction notes

Loading…