HOAt → tert-Butyl (2S)-2-{5-[(E)-3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzamido}-4-methylsulfanylbutyrate

HRID 1019031Notes

Reaction equation

HRID 1019031 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.[C:38]([O:42][C:43](=[O:50])[C@H:44]([CH2:46][CH2:47][S:48][CH3:49])[NH2:45])([CH3:41])([CH3:40])[CH3:39].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:45][C@@H:44]([CH2:46][CH2:47][S:48][CH3:49])[C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:50])=[O:15])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 181649HOAtHCID 7010638Tert-butyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 18399494pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

Product 1

HCID 9915176tert-Butyl (2S)-2-{5-[(E)-3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzamido}-4-methylsulfanylbutyrateYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of pentafluorophenyl 5-[(E)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate (0.36 g, 0.7 mmol), L-methionine-tert-butyl ester(0.173 g, 0.84 mmol) and 1-hydroxy-7-azabenzotriazole (0.1 g, 0.73 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 solution and saturated brine and evaporated to dryness. The residue was then purified by flash chromatography eluting with dichloromethane/ethanol (97/3) to give the title compound. Yield: 50%

Workup

  1. customAfter evaporation of the solvent
  2. washwashed with 5% sodium hydrogen carbonate solution and saturated brine
  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-2c6198e6721d4cd880cafbd8e8cd019b
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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