4-Chlorobenzenesulfonyl chloride → (2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methoxybenzyl)amino]-4-methylpentanoic acid amide

HRID 507298Notes

Reaction equation

HRID 507298 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[O:11])=[CH:5][CH:4]=1.CCN(CC)CC.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:8]([C@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([NH2:12])=[O:11])[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 59432820(2R)-2-(4-Methoxybenzylamino)-4-methylpentanoic acid amide

Product 1

HCID 9867067(2R)-2-[N-(4-Chlorobenzenesulfonyl)-N-(4-methoxybenzyl)amino]-4-methylpentanoic acid amideYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-[N-(4-Methoxybenzyl)amino]-4-methylpentanoic acid amide (3.57 g, 14.3 mmol) was dissolved in CH2Cl2 (100 mL) and treated with Et3N (4.2 mL, 29 mmol) and 4-chlorobenzenesulfonyl chloride (3.6 g, 17 mmol) at rt for 18 h. The solvents were removed and the residue was taken into EtOAc (500 mL). The organic solution was washed with H2O, brine, dried over MgSO4, and concentrated. The resulting material was then further purified by flash chromatography (SiO2, 1% MeOH/CH2Cl2) to afford the title compound (2.4 g) as a slightly colored solid in 40% yield. MS (ESI), (M−H)− 422.9; 1H NMR (CDCl3) δ 7.63 (d, 2H, J=7.0), 7.42 (d, 2H, J=7.0), 7.25 (d, 2H, J=8.0), 6.79 (d, 2H, J=8.0), 6.25 (br s, 1H), 5.35 (br s, 1H), 4.36 (dd, 2H, J=5.0, 15), 4.26 (t, 1H, J=7.2), 3.78 (s, 3H), 1.83 (m, 1H), 1.18-1.34 (m, 2H), 0.75 (d, 3H, J=7.0), 0.67 (d, 3H, J=7.0); IR (KBr) 3480, 2959, 1693, 1674, 1514, 1333, 1158 cm−1.

Workup

  1. customThe solvents were removed
  2. washThe organic solution was washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting material was then further purified by flash chromatography (SiO2, 1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-63106d292e8e4a4d823a9ba4a2df9e7e
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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