Water → 1-O-benzyl-2-(carboxymethylthio)glycerol

HRID 1636287Notes

Reaction equation

HRID 1636287 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:19][O:20][Si](C(C)(C)C)(C)C)[O:11][S:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[K+]>CO>[CH2:1]([O:8][CH2:9][CH:10]([CH2:19][OH:20])[O:11][S:12][CH2:13][C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 193508051-O-benzyl-3-O-t-butyldimethylsilyl-2-(ethoxycarbonylmethylthio)glycerol

Product 1

HCID 193508451-O-benzyl-2-(carboxymethylthio)glycerolYield 91.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-O-Benzyl-3-O-t-butyldimethylsilyl-2-(ethoxycarbonylmethylthio)glycerol (1 g) was added to a solvent mixture of water (8 ml) and methanol (16 ml), and potassium hydroxide (1 g) added thereto and the mixture stirred overnight at room temperature. The reaction mixture was extracted with ethyl ether twice to remove the impurities, and the pH of the extract was adjusted to 1 to 2 with 6N hydrochloric acid. Then the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the desired product (0.6 g).

Workup

  1. additionadded
  2. extractionThe reaction mixture was extracted with ethyl ether twice
  3. customto remove the impurities
  4. extractionThen the mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b5e0dc59c210428f80e8f3dce701596c
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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