HCID 68833152, compound → HCID 68833440, compound

HRID 1454105Notes

Reaction equation

HRID 1454105 reaction equation
[NH2:1][C:2](=[O:22])[CH2:3][CH:4]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6]>C(O)C.[Pd]>[NH2:1][C:2](=[O:22])[CH2:3][CH:4]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 68833152HCID 68833152, compound

Product 1

HCID 68833440HCID 68833440, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of benzyl 4-amino-2-(4-hydroxyphenyl)-4-oxobutanoate (327 mg, 1.09 mmol) and palladium on charcol (10%, 50 mg) in ethanol (30 mL) was stirred under a 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 white solid (229 mg, 100%). LC/MS: 0.81 min; z/e 210, calcd (M+1) 210. 1H NMR (400 MHz: DMSO-d6): 11.9 (1H), 9.10 (1H), 7.10 (1H), 6.85 (2H), 6.55 (1H), 6.50 (2H), 3.60 (1H), 2.60 (1H), 2.15 (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-8a2c90f53a984e69a37d9ad4fb335a9b
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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