HCID 59166705, compound → HCID 59166713, compound

HRID 1442682Notes

Reaction equation

HRID 1442682 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:33]=[CH:32][C:8]2[N:9]=[C:10]([C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23]CC4C=CC=CC=4)=[C:19]([CH3:31])[CH:18]=3)([CH2:15][CH3:16])[CH2:13][CH3:14])[O:11][C:7]=2[CH:6]=1)=[O:4]>CO.C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:33]=[CH:32][C:8]2[N:9]=[C:10]([C:12]([CH2:13][CH3:14])([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH3:31])[CH:18]=3)[CH2:15][CH3:16])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 1

HCID 59166705HCID 59166705, compound

Product 1

HCID 59166713HCID 59166713, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[1-(4-benzyloxy-3-methyl-phenyl)-1-ethyl-propyl]-benzooxazole-6-carboxylic acid methyl ester (1.50 g, 3.38 mmol) in MeOH (20 mL) is added a slurry of Pd—C (150 mg, 10%) in THF (20 mL) at RT. The resulting mixture is stirred under hydrogen balloon pressure for 12 h. The mixture is filtered through a pad of celite, and the filtrate is concentrated. The residue is purified with 20% EtOAc/Hex to afford the title compound (1.20 g, 100%). H-NMR (ppm, CDCl3) δ: 8.11 (1H, s), 8.03 (1H, dd, J=1.8, 8.4 Hz), 7.73 (1H, d, J=8.4 Hz), 6.97 (1H, d, J=2.2 Hz), 6.92 (1H, dd, J=2.2, 8.4 Hz), 6.70 (1H, d, J=8.4 Hz), 3.93 (3H, s), 2.40 (2H, q, J=7.5 Hz), 2.30 (2H, q, J=7.5 Hz), 2.20 (3H, s), 0.76 (6H, t, J=7.5 Hz).

Workup

  1. filtrationThe mixture is filtered through a pad of celite
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified with 20% EtOAc/Hex

Sources & evidence

ORD record
ord-014b33b33e2543349f06ef1661473b01
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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