Ethanol → HCID 18790108, compound

HRID 1107169Notes

Reaction equation

HRID 1107169 reaction equation
[OH:1][NH:2][C:3](=[O:27])[CH2:4][CH:5]([S:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1.C(O)C>C(Cl)Cl>[OH:1][NH:2][C:3](=[O:27])[CH2:4][CH:5]([S:16]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)=[O:36])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 70297m-Chloroperbenzoic acidHCID 10810381HCID 10810381, compound

Product 1

HCID 18790108HCID 18790108, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-N-hydroxy-3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanamide (1.26 g, 3.24 mmol) in anhydrous CH2Cl2 (20 mL) at 0° C. is added m-CPBA (0.56 g, 3.24 mmol) in one portion. The mixture is stirred for 10 minutes after which TLC analysis indicated complete reaction. Ethanol (2 mL) is added and the mixture is partitioned between water (100 mL) and EtOAc (100 mL). Aqueous layer is extracted with EtOAc (2×50 mL) and combined organic phases are washed successively with 5% aqueous Na2S2O3 (50 mL), water (50 mL), 5% aqueous NaHCO3 (50 mL), water (50 mL) and brine (50 mL) then dried over MgSO4 and concentrated. The resulting yellow oil is chromatographed on silica gel (CH2Cl2 →2% MeOH/CH2Cl2 →5% MeOH/CH2Cl2) to afford 0.5 g of (±)-N-hydroxy-3-(3,4-dimethoxyphenyl)sulfinyl-7-phenylheptanamide (38%) as a mixture (2:1) of diastereomers in the form of a white foam. TLC analysis [CH2Cl2 /MeOH, 19:1, Rf (sulfide)=0.20, Rf (sulfoxide)=0.10]. 1H NMR (300 MHz, d6 -DMSO) δ 1.35-1.72 (m, 6H), 1.88-2.20 (m, 2H), 2.49 (m, 2H), 3.05 (m, 1H), 3.78 (br s, 6H), 7.0-7.18 (m, 6H), 7.22 (m, 2H), 8.80 (m, 1H), 10.49 (m,1H) ppm. Mass spectrum (FAB) m/z 406 (M+H)+.

Workup

  1. customreaction
  2. customthe mixture is partitioned between water (100 mL) and EtOAc (100 mL)
  3. extractionAqueous layer is extracted with EtOAc (2×50 mL)
  4. washare washed successively with 5% aqueous Na2S2O3 (50 mL), water (50 mL), 5% aqueous NaHCO3 (50 mL), water (50 mL) and brine (50 mL)
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated
  7. customThe resulting yellow oil is chromatographed on silica gel (CH2Cl2 →2% MeOH/CH2Cl2 →5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d6a53ccd5c6d468880fcef9154f3d1ba
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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