4-Chlorobenzenesulfonyl chloride → tert-butyl (2R)-2-{[(4-chlorophenyl)sulfonyl]amino}propanoate

HRID 1892832Notes

Reaction equation

HRID 1892832 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[C@@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:9][C@H:8]([CH3:10])[C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 16211919D-Alanine tert-butyl ester hydrochloride

Product 1

HCID 66934865tert-butyl (2R)-2-{[(4-chlorophenyl)sulfonyl]amino}propanoateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To D-alanine tert-butyl ester hydrochloride (1 g) in methylene chloride (35 ml) solution, triethylamine (1.7 ml) and 4-chlorobenzenesulfonyl chloride (1.1 g) were added under ice cooling and the mixture was stirred at room temperature for 2 hours. The methylene chloride was distilled off in vacuo, then the residue was diluted with ethyl acetate. The obtained solution was successively washed with distilled water, saturated potassium hydrogensulfate aqueous solution, and saturated saline, dried over with anhydrous sodium sulfate, then concentrated. The residue was recrystallized from ethyl acetate/hexane to obtain the title compound (1.47 g).

Workup

  1. distillationThe methylene chloride was distilled off in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washThe obtained solution was successively washed with distilled water, saturated potassium hydrogensulfate aqueous solution, and saturated saline
  4. dry with materialdried over with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1b4d028194824a52bbf206e10939c0b3
Source dataset
uspto-grants-2013_08
Patent number
US08507714B2

Reaction notes

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