Trifluoroacetic acid → HCID 67260076, compound

HRID 1027603Notes

Reaction equation

HRID 1027603 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]([OH:38])[CH2:10][NH:11][C:12](=[O:37])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:23][C:22]([C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=3)([C:24]([F:27])([F:26])[F:25])[O:21][N:20]=2)=[CH:15][C:14]=1[CH3:36])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH2:8][CH:9]([OH:38])[CH2:10][NH:11][C:12](=[O:37])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:23][C:22]([C:28]3[CH:29]=[C:30]([Cl:35])[CH:31]=[C:32]([Cl:34])[CH:33]=3)([C:24]([F:26])([F:27])[F:25])[O:21][N:20]=2)=[CH:15][C:14]=1[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67246577HCID 67246577, compound

Product 1

HCID 67260076HCID 67260076, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3{4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoylamino}-2-hydroxy-propyl)-carbamic acid tert-butyl ester (0.2 g) in dichloromethane (10 ml) was cooled to 0° C., treated with trifluoroacetic acid (0.5 ml) and stirred for 10 h. The reaction mixture was concentrated in vacuo and diluted with dichloromethane (50 ml), washed with saturated aqueous solution of sodium bicarbonate (20 ml) and finally with water (2×20 ml). The organic layer was separated, dried over sodium sulfate and concentrated to give the title compound (0.13 g). LCMS (Method G) 2.84 min, MH+ 490. 1HNMR (CDCl3, 400 MHz): 8.05 (t, 1H), 7.81 (m, 1H), 7.80 (brs, 2H), 7.59 (m, 4H), 7.48 (d, 1H), 4.36 (dd, 2H), 3.85 (m, 2H), 3.28 (m, 2H), 2.50 (m, 1H), 2.37 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane (50 ml)
  3. washwashed with saturated aqueous solution of sodium bicarbonate (20 ml) and finally with water (2×20 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ec7239f9e4945e6a1b0101615642623
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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