Hydrochloric Acid → (2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amide

HRID 507300Notes

Reaction equation

HRID 507300 reaction equation
COC1C=CC(CN[C@H](CC(C)C)C(N)=O)=CC=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH:40]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:41]([NH2:43])=[O:42])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][CH:32]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>CO.[Pd]>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([N:29]([C@H:40]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:41]([NH2:43])=[O:42])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)(=[O:27])=[O:28])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 59432820(2R)-2-(4-Methoxybenzylamino)-4-methylpentanoic acid amideHCID 772384772-[N-(4-Chlorobenzenesulfonyl)-N-(4-nitrobenzyl)amino]-4-methylpentanoic acid amide

Product 1

HCID 59001017(2R)-2-[(4-aminobenzyl)-(4-chloro-benzenesulfonyl)amino]-4-methyl-pentanoic acid amideYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2R)-(2-[N-(4-Chlorobenzenesulfonyl)-N-(4-nitrobenzyl)amino]-4-methylpentanoic acid amide (Compound of Example 24; prepared as described in Reaction Scheme 1; 2.8 g, 6.6 mmol) was suspended with 10% Pd/C (1 g) and conc. HCl (1 mL) in MeOH (100 mL) and placed under a hydrogen atmosphere at 40 psi for 1 h. The suspension was filtered through Celite and then concentrated to give the title compound as a tan solid (2.4 g, 88% yield). MS (ESI), (M+H)+ 410.1; 1H NMR (CDCl3) δ 7.80 (d, 2H, J=8.5), 7.63 (d, 2H, J=8.5), 7.52 (br s, 1H), 7.46 (d, 1H, J=8.0), 7.26 (d, 1H, J=8.0), 7.02 (br s, 1H), 4.70 (dd, 2H, J=50, 18), 4.30-4.41 (m, 1H), 3.67 (br s, 2H), 1.28-1.33 (m, 3H), 0.86 (d, 3H, J=7.0), 0.57 (d, 3H, J=7.0).

Workup

  1. filtrationThe suspension was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-49e3d1ebdad74744985504d4f45bd6d7
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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