Hydrochloric Acid → HCID 14292107, compound

HRID 1089901Notes

Reaction equation

HRID 1089901 reaction equation
[OH:1][C@H:2]([CH2:6][OH:7])[CH2:3][C:4]#[N:5].[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9].Cl>N1C=CC=CC=1.C(Cl)Cl>[OH:1][C@H:2]([CH2:6][O:7][S:8]([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH2:3][C:4]#[N:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 24820172HCID 24820172, compound

Product 1

HCID 14292107HCID 14292107, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(3S)-3,4-Dihydroxybutyronitrile (161.8 g, 1.6 mol) was dissolved in pyridine (260 ml). To the resulting solution, a solution of tosyl chloride (396.6 g) in methylene chloride (1.6 liters) was added at 0° C. and stirred at 0° C. for 5 hours. Then, the pH of the mixture was adjusted at 2 with 6N hydrochloric acid, and the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (85.9 g). Yield, 70 %.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated off
  4. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8e878f2944744f71a1daf88bd36c095a
Source dataset
uspto-grants-1992_01
Patent number
US05079382

Reaction notes

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