HCID 89544105, compound → HCID 89544134, compound

HRID 2203452Notes

Reaction equation

HRID 2203452 reaction equation
[CH:1]([N:14]1[C:18]2[CH:19]=[C:20]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=3[O:30]CC3C=CC=CC=3)[CH:21]=[CH:22][C:17]=2[O:16][C:15]1=[O:38])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C.CO>[CH:1]([N:14]1[C:18]2[CH:19]=[C:20]([C:23]3[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=3[OH:30])[CH:21]=[CH:22][C:17]=2[O:16][C:15]1=[O:38])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 89544105HCID 89544105, compound

Product 1

HCID 89544134HCID 89544134, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 3-benzhydryl-5-(2-(benzyloxy)-5-methylphenyl)benzo[d]oxazol-2(3H)-one (1.0 g, 2.0 mmol) and palladium on activated charcoal (10% w/w, 0.20 g) in ethyl acetate/methanol (1:1 v/v, 20 mL) was stirred under an atmosphere of hydrogen (1 atm) for 16 h. The reaction mixture was filtered through a pad of diatomaceous earth and the pad was washed with ethyl acetate/methanol (1:1 v/v, 20 mL). The filtrate and washes were combined and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-65% gradient of ethyl acetate in hexanes to afford 3-benzhydryl-5-(2-hydroxy-5-methylphenyl)benzo[d]oxazol-2(3H)-one as a colorless solid in 98% yield (0.80 g): 1H NMR (300 MHz, CDCl3) δ 7.38-7.32 (m, 6H), 7.30-7.24 (m, 5H), 7.17-7.12 (m, 1H), 6.99 (dd, J=8.2, 1.6 Hz, 1H), 6.84 (s, 1H), 6.79-6.73 (m, 2H), 6.51 (s, 1H), 4.68 (s, 1H), 2.24 (s, 3H); MS (ES+) m/z 407.8 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washthe pad was washed with ethyl acetate/methanol (1:1 v/v, 20 mL)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluting with a 20-65% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ecb1bf5b679d48fdbd92f2b4ed4d862b
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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