Dimethylamine → (2R)-2-{(4-Chlorobenzenesulfonyl)-[4-(2-dimethylamino-acetylamino)-benzyl]-amino}-4-methyl-pentanoic acid amide

HRID 1893854Notes

Reaction equation

HRID 1893854 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:31]=[CH:30][C:9]([CH2:10][N:11]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])=[CH:8][CH:7]=1)=[O:4].[CH3:32][NH:33][CH3:34]>C(Cl)Cl.C1COCC1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:11]([CH2:10][C:9]2[CH:30]=[CH:31][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:33]([CH3:34])[CH3:32])=[CH:7][CH:8]=2)[C@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([NH2:15])=[O:14])(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 10218145(2R)-2-[[4-(2-Bromo-acetylamino)-benzyl]-(4-chlorobenzenesulfonyl)-amino]-4-methyl-pentanoic acid amide

Product 1

HCID 10217720(2R)-2-{(4-Chlorobenzenesulfonyl)-[4-(2-dimethylamino-acetylamino)-benzyl]-amino}-4-methyl-pentanoic acid amideYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-[[4-(2-bromo-acetylamino)-benzyl]-(4-chlorobenzenesulfonyl)-amino]-4-methyl-pentanoic acid amide (41 mg, 0.77 mmol) in CH2Cl2 (2 mL) was added excess 2.0 M dimethylamine in THF. The reaction mixture was stirred overnight. The solvent was removed in vacuo. Purification by flash chromatography (SiO2, 10% MeOH/CH2Cl2) afforded the title compound (24 mg) in 63% yield. MS (ESI), (M+H)+495.14, 1H NMR (CDCl3, 400 MHz) δ 8.85 (s, 1H), 8.02 (d, 2H, J=8.0), 7.75 (d, 2H, J=8.0), 7.38 (d, 2H, J=8.0), 7.29 (d, 2H, J=8.0), 6.23 (br s, 1H), 5.39 (br s, 1H), 4.62 (m, 4H), 3.25 (t, 1H, J=6.0), 2.95 (s, 6H), 1.95 (m, 1H), 1.60 (m, 2H), 0.98 (d, 3H, J=7.0), 0.94 (d, 3H, J=7.0)

Workup

  1. customThe solvent was removed in vacuo
  2. customPurification by flash chromatography (SiO2, 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2ae1007d508f451682f263afba643d58
Source dataset
uspto-grants-2013_08
Patent number
US08513253B2

Reaction notes

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