HCID 58964594, compound → HCID 24284802, compound

HRID 1160103Notes

Reaction equation

HRID 1160103 reaction equation
C([O:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[O:11])C1C=CC=CC=1>CO>[OH:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=1)=[O:11]

Participants

3

Reactant 1

HCID 58964594HCID 58964594, compound

Product 1

HCID 24284802HCID 24284802, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 1 L pressure vessel was added crude 2-Benzyloxy-N-(3-trifluoromethyl-phenyl)-acetamide (˜10 g) and methanol (400 mL). The solution was purged with N2. 10% Pd/C (1.1 g) was added. The vessel was placed under H2 atmosphere at 50 psi for 2.5 h. LC/MS analysis shows only partial hydrogenolysis of the benzyl ether, so Pd(OH)2H2O (2 g) was added and the vessel is placed again under H2 atmosphere at 50 psi for 2.5 h. The reaction mixture was filtered through a pad of Celite and concentrated to give a brown oil. The crude material was purified via flash chromatography (1:1 EtOAc/Hexanes) to give 2-hydroxy-N-(3-trifluoromethyl-phenyl)-acetamide as a white solid (5.27 g, 84% yield, two steps). LC/MSD (HP Series 1100 MSD) Expected MW: 219.05, Observed M+H, 220.0, Retention time: 1.22. 1H-NMR, DMSO-d6, Varian 400 MHz δ 10.07 (s, 1H), 8.22 (s, 1H), 7.97 (dd, 1H), 7.55 (t, 1H), 7.41 (m, 1H), 5.76 (t, 1H), 4.03 (d, 2H) ppm.

Workup

  1. customThe solution was purged with N2
  2. addition10% Pd/C (1.1 g) was added
  3. additionwas added
  4. waitthe vessel is placed again under H2 atmosphere at 50 psi for 2.5 h
  5. filtrationThe reaction mixture was filtered through a pad of Celite
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThe crude material was purified via flash chromatography (1:1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-64540826b3044025b93f13c9b8d7cd03
Source dataset
uspto-grants-2010_10
Patent number
US07816353B2

Reaction notes

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