HCID 86753075, compound → HCID 6539658, compound

HRID 2393105Notes

Reaction equation

HRID 2393105 reaction equation
C([O:8][NH:9][C:10](=[O:25])[C@H:11]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:12]([CH3:14])[CH3:13])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[OH:8][NH:9][C:10](=[O:25])[C@H:11]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH:12]([CH3:13])[CH3:14]

Participants

4

Reactant 1

HCID 86753075HCID 86753075, compound

Product 1

HCID 6539658HCID 6539658, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of N-benzyloxy-2(R)-[(benzenesulfonyl)amino]-3-methyl butanamide (100 mg, 0.280 mmol) and Pearlman's catalyst (25 mg) in MeOH (10 mL) is hydrogenated at 1 atmosphere for 3 hours. The mixture is filtered through celite, and the filtrate is concentrated. The desired material is crystallized from EtOAc/pentane to give 61 mg (80%) of the title compound as a crystalline solid. mp 154°-155° C.; IR (mineral oil) 3268, 2925, 2954, 2881, 2855, 1636, 1449, 1336, 1165, 694 cm-1; 1H NMR (300 MHz, DMSO-d6) δ10.53, 8.83, 7.98, 7.76, 7.50-7.65, 3.28, 1.65-1.85, 0.74, 0.70; MS (EI) m/z 272; Analysis: C, 48.37; H, 6.07; N, 10.14.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate is concentrated
  3. customThe desired material is crystallized from EtOAc/pentane

Sources & evidence

ORD record
ord-cda8435374be4a70900d249d3191f124
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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