4-Chlorobenzenesulfonyl chloride → (2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amide

HRID 507291

Reaction equation

HRID 507291 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]([NH2:10])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].CCN(CC)CC.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:2][C@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[C:8]([NH2:10])=[O:9])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochloride

Product 1

HCID 59001058(2R)-2-(4-Chlorobenzenesulfonylamino)-4-methylpentanoic acid amideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (D)-leucinamide hydrochloride (0.25 g, 1.5 mmol), and Et3N (0.43 mL, 3.0 mmol) in CH2Cl2 (150 mL) was added 4-chlorobenzenesulfonyl chloride (380 mg, 1.8 mmol). The resulting solution was stirred at rt for 18 h. The reaction was then diluted with CH2Cl2 (200 mL) and washed with H2O, 0.5 N HCl, brine, and dried over MgSO4, to afford the titled compound (410 mg) as a white solid in 90% yield. MS (ESI), (M+H)+ 305.2; 1H NMR (DMSO-d6) δ 7.77 (d, 2H, J=8.7), 7.62 (d, 2H, J=8.7), 6.90 (br s, 1H), 3.67 (m, 1H), 1.54 (m, 1H), 1.31 (m, 2H), 0.81 (d, 3H, J=7.0), 0.71 (d, 3H, J=7.0).

Workup

  1. washwashed with H2O, 0.5 N HCl, brine
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9bb8f87368bb4c3da831aca7229eeb11
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Linked notes

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