Hydrochloric Acid → HCID 15037028, compound

HRID 1089902Notes

Reaction equation

HRID 1089902 reaction equation
[OH:1][C@H:2]([CH2:6][OH:7])[CH2:3][C:4]#[N:5].[S:8](Cl)([CH3:11])(=[O:10])=[O:9].Cl>N1C=CC=CC=1>[OH:1][C@H:2]([CH2:6][O:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH2:3][C:4]#[N:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 24820172HCID 24820172, compound

Product 1

HCID 15037028HCID 15037028, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(3S)-3,4-Dihydroxybutyronitrile (8.0 g, 79.1 mmol), pyridine (19.1 ml) and mesyl chloride (7.33 ml) were mixed at 0° C. for 6 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 (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (8.1 g). Yield, 57 %.

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 (acetone:chloroform=5:95)

Sources & evidence

ORD record
ord-1078e3e6bf9349b6bbce8a54e672c352
Source dataset
uspto-grants-1992_01
Patent number
US05079382

Reaction notes

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