Hydrochloric Acid → HCID 14292107, compound

HRID 1089900Notes

Reaction equation

HRID 1089900 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>[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

5

Reactant 3

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

Product 1

HCID 14292107HCID 14292107, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3S)-3,4-Dihydroxybutyronitrile (43.1 g, 426 mmol), pyridine (240 ml) and tosyl chloride (119.5 g) were mixed at 0° C. for 4 hours. The mixture was poured in ice-cooled 1N hydrochloric acid and stirred, followed by extraction with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off with an evaporator. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (3S)-3-hydroxy-4-p-toluenesulfonyloxybutyronitrile (87.0 g, 340 mmol). Yield, 80 %.

Workup

  1. additionThe mixture was poured in ice-
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated off with an evaporator
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1b34ccb1446b49b99e0e9fc386603001
Source dataset
uspto-grants-1992_01
Patent number
US05079382

Reaction notes

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