Water → 4-benzyloxy-N-(3-cyclohexylphenyl)-3-methanesulfonylaminophenylacetamide

HRID 7064Notes

Reaction equation

HRID 7064 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:21]=2)=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].O>N1C=CC=CC=1>[CH2:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:21]=2)=[O:18])=[CH:3][C:2]=1[NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 220196013-Amino-4-benzyloxy-N-(3-cyclohexylphenyl)phenylacetamide2×

Product 1

HCID 220196484-benzyloxy-N-(3-cyclohexylphenyl)-3-methanesulfonylaminophenylacetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Amino-4-benzyloxy-N-(3-cyclohexylphenyl)phenylacetamide (the compound of Example 33) (200 mg) is dissolved in pyridine (5 ml), and thereto is added dropwise methanesulfonyl chloride (111 mg), and the mixture is stirred for 0.5 hour. Water is added to the mixture, and the mixture is extracted with ethyl acetate. The organic layer is dried under sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-benzyloxy-N-(3-cyclohexylphenyl)-3-methanesulfonylaminophenyl-acetamide (200 mg). This product is dissolved in ethanol (10 ml), and thereto is added 10% palladium on carbon (20 mg). The mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 10% chloroform/methanol) to give the desired compound (120 mg).

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. customThe organic layer is dried under sodium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4fca6104173e474c88751c15eb8cd6a3
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Reaction notes

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