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

HRID 554778Notes

Reaction equation

HRID 554778 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-23e36cb5418444ff9495c7d7336c4ea8
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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