DL-Homoserine → (RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide

HRID 266354

Reaction equation

HRID 266354 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][OH:8])[C:3]([OH:5])=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O.C1COCC1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][CH:2]2[CH2:6][CH2:7][O:8][C:3]2=[O:5])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 779DL-HomoserineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 19032731(RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolideYield 60.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(RS)-2-amino-4-hydroxybutanoic acid (2.0438 g) was dissolved in water (20 ml). The solution was cooled to 0° C., and potassium carbonate (5.217 g) and ethyl acetate (20 ml) were added. Then, p-chlorobenzenesulfonyl chloride (9.0536 g) and THF (2 ml) were added, and the whole was stirred overnight. After the reaction was completed, the ethyl acetate layer was separated. The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated to give a crude product. The crude product was purified by silica gel column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide (2.8674 g).

Workup

  1. customthe ethyl acetate layer was separated
  2. extractionextracted with ethyl acetate
  3. concentrationThe combined ethyl acetate layers were concentrated
  4. customto give a crude product
  5. customThe crude product was purified by silica gel column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-b9c6c5a45e164ac8aa66d3c6f2f83ebc
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Linked notes

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