Water → HCID 53962617, compound

HRID 2226586Notes

Reaction equation

HRID 2226586 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C@@H:5]([O:9][C:10](=[O:12])[CH3:11])[CH2:6][CH2:7][OH:8])[CH3:2].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(OCC)(=O)C.O>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:13])[C@@H:5]([O:9][C:10](=[O:12])[CH3:11])[CH2:6][CH2:7][O:8][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:14])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 11171486ethyl (2S)-2-acetyloxy-4-hydroxybutanoate

Product 1

HCID 53962617HCID 53962617, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

(S)-2-Acetoxy-4-hydroxybutanoic acid ethyl ester (0.5 g, 2.6 mmol) in pyridine (1 ml) was added to a solution of (4-methylphenyl)sulphonyl chloride (0.53 g, 2.76 mmol) in pyridine (1 ml) at 5°. After 16 h at 5° ethyl acetate and water were added, the organic layer was separated, washed with hydrochloric acid (2N), dried (MgSO4) and the solvent evaporated to give the sub-title ester (0.8 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with hydrochloric acid (2N)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-cd869c0f7fed44b5825da87b3b133623
Source dataset
uspto-grants-1994_09
Patent number
US05348978

Reaction notes

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