Water → Methyl 3-(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionate

HRID 2110999Notes

Reaction equation

HRID 2110999 reaction equation
ClC1C=CC=CC=1C([N:10]([C:14]1[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=2)=[N:16][O:17][CH:18]=1)[C:11](=[O:13])[O-:12])C.C(N([CH2:32][CH3:33])CC)C.[SH:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38].O.Cl[CH2:43][Cl:44]>>[Cl:44][C:43]1[CH:20]=[CH:19][CH:15]=[CH:14][C:18]=1[CH:32]([O:12][C:11]([NH:10][C:14]1[C:15]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][S:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:23][CH:24]=2)=[N:16][O:17][CH:18]=1)=[O:13])[CH3:33]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 18050Methyl 3-mercaptopropionateHCID 866074181-(2-Chlorophenyl)ethyl[3-(4-bromomethylphenyl)-isoxazolyl]carbamate

Product 1

HCID 11454331Methyl 3-(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionateYield 8.7%

Procedure

To a solution of 1-(2-chlorophenyl)ethyl[3-(4-bromomethylphenyl)-isoxazolyl]carbamate (615 mg, 1.41 mmol) in dichloromethane (18 ml) were added triethylamine (855 mg, 8.47 mmol) and methyl 3-mercaptopropionate (445 mg, 4.23 mmol), and the mixture was stirred overnight at room temperature. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the title compound (58.5 mg, 0.123 mmol, 8.7%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-d8a6249d48be4318b9279916b63aaf8d
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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