Allyl Mercaptan → HCID 10590430, compound

HRID 370512Notes

Reaction equation

HRID 370512 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 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, was dried over magnesium sulphate, 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 materialwas dried over magnesium sulphate
  4. customevaporated to dryness
  5. customchromatographed on silica gel
  6. washElution with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1119f7a09115436f87b8fc3d4f8aef84
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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