HCID 68833154, compound → HCID 68831353, compound

HRID 1454094Notes

Reaction equation

HRID 1454094 reaction equation
[NH2:1][C:2](=[O:22])[CH2:3][CH:4]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6]>C(O)C.[Pt](=O)=O>[NH2:1][C:2](=[O:22])[CH2:3][CH:4]([C:15]1[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 68833154HCID 68833154, compound

Product 1

HCID 68831353HCID 68831353, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A suspension of benzyl 4-amino-2-(4-bromophenyl)-4-oxobutanoate (1.53 g, 4.22 mmol) and platinum(IV) oxide (30 mg) in ethanol (100 mL) was stirred under an hydrogen atmosphere for 2 h. After replacement of hydrogen with nitrogen the crude reaction mixture was filtered through a thin pad of celite and the filtrate evaporated to dryness to give the title compound as a cream coloured solid (1.14 g, 100%). LC/MS: 2.36 min; z/e 272 and 274, calcd (M+1) 272 and 274. 1H NMR (400 MHz: DMSO-d6): 7.50 (2H), 7.30 (1H), 7.20 (2H), 6.80 (1H), 3.90 (1H), 2.80 (1H), 2.40 (1H).

Workup

  1. customAfter replacement of hydrogen with nitrogen the crude reaction mixture
  2. filtrationwas filtered through a thin pad of celite
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-dafc222024e74344bb381034d00c32ad
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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