Acetic Acid → HCID 57665940, compound

HRID 889747Notes

Reaction equation

HRID 889747 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[CH3:33][C:34](C1C=CC(C(F)(F)F)=CC=1)=O.C(O[BH3-])(=O)C.[Na+].C(O)(=O)C>ClCCCl>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:10]1[CH:11]=[C:12]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)[CH:13]=[C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18]([CH2:33][CH3:34])[CH2:17]2)[CH:15]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 23670382SodiumacetoxyborohydrideHCID 576660204-Methyl-2-(5-piperidin-3-yl-4'-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester

Product 1

HCID 57665940HCID 57665940, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (47 mg, 0.11 mmol), and 4-Trifluoromethylacetophenone (20 mg, 0.11 mmol), in 1,2 dichloroethane (0.7 ml) was added sodium acetoxyborohydride (29 mg, 0.14 mmol) and acetic acid (6.6 μl, 0.12 mmol). The reaction stirred at room temperature with little product. The reaction was heated at 50° C., then reflux over 48 hours. The solution was concentrated in vacuo, and purified by silica gel chromatography to give the above pictured by product. Calcd for C28H36F3NO2 (M+H) 475.59, Found 476.4.

Workup

  1. temperatureThe reaction was heated at 50° C.
  2. temperaturereflux over 48 hours
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by silica gel chromatography
  5. customto give the

Sources & evidence

ORD record
ord-72c8b3613c98430a8ddf1d840ee186fd
Source dataset
uspto-grants-2012_08
Patent number
US08252935B2

Reaction notes

Loading…