Water → HCID 15484980, compound

HRID 1251380Notes

Reaction equation

HRID 1251380 reaction equation
[OH:1][NH:2][C:3](=[O:22])[C:4]([S:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH2:23]>CO>[OH:1][NH:2][C:3](=[O:22])[C:4]([S:13]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)=[O:23])([CH3:12])[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 962WaterHCID 9948873HCID 9948873, compound

Product 1

HCID 15484980HCID 15484980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-hydroxy-2-(4-methoxy-phenylsulfanyl)-2-methyl-3-phenyl-propionamide (400 mg, 1.26 mol) in Example 1) was dissolved in methanol (100 ml) and 30% H2O (10 ml) was added. The reaction mixture was stirred for 48 hours at room temperature at which time it was cooled to 0° C. and quenched with saturated Na2SO3 (20 ml) solution. The reaction mixture became cloudy. It was stirred for 4 hours before it was concentrated in a room temperature water bath, diluted with water, extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated. The title compound isolated by silica gel column chromatography, eluting with 75% ethylacetate:hexane. Low melting solid. Yield: 220 mg (52%); MS: 334.1 (M+H)+; 1H NMR (300 MHz, CDCl3): d 1.11 (s, 2H), 1.22 (s, 3H), 3.84 (s, 3H), 7.00-7.61 (m, 9H).

Workup

  1. temperaturewas cooled to 0° C.
  2. customquenched with saturated Na2SO3 (20 ml) solution
  3. stirringIt was stirred for 4 hours before it
  4. concentrationwas concentrated in a room temperature water bath
  5. additiondiluted with water
  6. extractionextracted with CHCl3
  7. washwashed with H2O
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8b1299d2cdc24abca6999d295b3e2a44
Source dataset
uspto-grants-2002_01
Patent number
US06342508B1

Reaction notes

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