HOAt → (3S)-3-{5-[(Z)-3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzamido}-5-methylsulfanyl-1-phenyl-2-pentanone

HRID 1019053Notes

Reaction equation

HRID 1019053 reaction equation
[N:1]1([CH2:6]/[CH:7]=[CH:8]\[C:9]2[CH:10]=[CH:11][C:12]([CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[C:13]([CH:28]=2)[C:14](OC2C(F)=C(F)C(F)=C(F)C=2F)=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH3:38][S:39][CH2:40][CH2:41][C@H:42]([NH2:52])[C:43](=[O:51])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.ON1C2N=CC=CC=2N=N1>CN(C=O)C>[N:1]1([CH2:6]/[CH:7]=[CH:8]\[C:9]2[CH:10]=[CH:11][C:12]([CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[C:13]([CH:28]=2)[C:14]([NH:52][C@@H:42]([CH2:41][CH2:40][S:39][CH3:38])[C:43](=[O:51])[CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 181649HOAtHCID 57166858(3S)-5-methylsulfanyl-2-oxo-1-phenylpentan-3amineHCID 86758617pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

Product 1

HCID 70159566(3S)-3-{5-[(Z)-3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzamido}-5-methylsulfanyl-1-phenyl-2-pentanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate (0.25 g, 0.5 mmol), (3S)-5-methylsulfanyl-2-oxo-1-phenylpentan-3amine (0.16 g, 0.6 mmol), 1-hydroxy-7-azabenzotriazole (0.075 g, 0.55 mmol) in DMF (2 ml) was stirred at ambient temperature overnight. After evaporation of the solvent, the residue was taken up in ethyl acetate, washed with 5% sodium hydrogen carbonate and saturated sodium chloride and evaporated to dryness. The residue was then purified by flash chromatography eluting with dichloromethane/ethanol (97/3) to give the title compound which was isolated as the hydrochloride salt by treatment with HCl/ether. Yield: 70%

Workup

  1. customAfter evaporation of the solvent
  2. washwashed with 5% sodium hydrogen carbonate and saturated sodium chloride
  3. customevaporated to dryness
  4. customThe residue was then purified by flash chromatography
  5. washeluting with dichloromethane/ethanol (97/3)

Sources & evidence

ORD record
ord-7d1fb8c8a5ea4cdf871b98a3fa8d822c
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

Loading…