Allyl Mercaptan → HCID 10590430, compound

HRID 622815Notes

Reaction equation

HRID 622815 reaction equation
[CH2:1]([SH:4])[CH:2]=[CH2:3].[OH-].[Na+].C(O[CH:11]1[NH:14][C:13](=[O:15])[C@H:12]1[C@H:16]([O:18][Si:19]([CH3:25])([CH3:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:17])(=O)C>O.CO>[CH2:1]([S:4][C@H:11]1[NH:14][C:13](=[O:15])[C@@H:12]1[C@H:16]([O:18][Si:19]([CH3:24])([CH3:25])[C:20]([CH3:22])([CH3:21])[CH3:23])[CH3:17])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 13367Allyl MercaptanHCID 14798Sodium HydroxideHCID 13073889HCID 13073889, compound

Product 1

HCID 10590430HCID 10590430, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1.14 ml of allyl mercaptan (70%) and 0.4 g of sodium hydroxide in 25 ml of water under an argon atmosphere was added a solution of 2.87 g of 4-acetoxy-3(S)-[1(R)-{dimethyl-(2-methylprop-2-yl)silyloxy}ethyl]-azetidin-2-one in 10 ml of methanol. After 30 minutes, the mixture was partitioned between dichloromethane and water. The separated organic layer was washed with water, dried over MgSO4, evaporated to dryness, and then chromatographed on silica gel. Elution with ethyl acetate-hexane mixtures afforded 1.8 g of the title compound as white crystals.

Workup

  1. customthe mixture was partitioned between dichloromethane and water
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customchromatographed on silica gel
  6. washElution with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-09d0b1c309f74dc096959149bcdac9c4
Source dataset
uspto-grants-1988_09
Patent number
US04772692

Reaction notes

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