4-Chlorobenzenesulfonyl chloride → Methyl 2-(4-chlorophenylsulfonamido)butanoate

HRID 15725

Reaction equation

HRID 15725 reaction equation
Cl.[NH2:2][CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:2][CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 13283515Methyl 2-aminobutanoate hydrochloride

Product 1

HCID 50739459Methyl 2-(4-chlorophenylsulfonamido)butanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-aminobutanoate hydrochloride 56 (25 g, 0.163 mol) was suspended in CH2Cl2 (100 mL) and triethylamine (50 mL) and 4-chlorobenzenesulfonyl chloride (37.8 g, 1.1 eq) were added to the mixture. The mixture was stirred at room temperature overnight. Diluted with 200 mL of CH2Cl2 and washed with water (3×50 mL), sat. NaHCO3 (2×50 mL), brine (50 mL) and dried (MgSO4). The solvent was removed by rotary evaporation to give the product 57 as a yellow oil. LCMS 292.0 (M+H).

Workup

  1. washwashed with water (3×50 mL), sat. NaHCO3 (2×50 mL), brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-bd35a0be3e80496ca7c11048f53668f9
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Linked notes

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