Potassium Carbonate → HCID 53782287, compound

HRID 1781957Notes

Reaction equation

HRID 1781957 reaction equation
[NH2:1][C@@H:2]([CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:40][C:41]([O:43][CH3:44])=[O:42]>CN(C)C=O.C(OCC)(=O)C>[CH3:44][O:43][C:41](=[O:42])[CH2:40][NH:1][C@@H:2]([CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:16]([F:17])([F:18])[F:19])[CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 44346694Benzeneethanamine, α-[[[3,5-bis(trifluoromethyl)phenyl]methoxy]methyl]-β-phenyl-, (S)-

Product 1

HCID 53782287HCID 53782287, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-amino-1-((3,5-bis(trifluoromethyl) phenyl)methyloxy)-3,3-diphenylpropane (8.6 g, Example 1i) and anhydrous K2CO3 (13.0 g)in dimethylformamide (50 ml) was added methyl bromoacetate (4.5 ml). The reaction was stirred at room temperature for 0.75 h then diluted with ethyl acetate (200 ml) and washed with water (4×100 ml), brine (100 ml), dried over MgSO4 and evaporated to dryness. The residual oil was purified on silica gel eluting with petroleum ether-ethyl acetate mixtures to give (S)-N-(1-((3,5-bis(trifluoromethyl)phenyl) methyloxy)-3,3-diphenylprop-2-yl)glycine methyl ester as an oil (7.61 g) 1H NMR (360 MHz, CDCl3) δ7.77 (1H, s), 7.71 (2H, s), 7.42 (2H, d, J=7.4 Hz), 7.33-7.13 (8H, m), 4.44 (2H, s), 4.12 (1H, d, J=7.2 Hz), 3.73-3.69 (1H, m), 3.63 (3H, s), 3.57-3.52 (1H, m), 3.53 (2H, d, J=6.7 Hz) and 3.44-3.36 (1H, m).

Workup

  1. washwashed with water (4×100 ml), brine (100 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residual oil was purified on silica gel eluting with petroleum ether-ethyl acetate mixtures

Sources & evidence

ORD record
ord-2f9111900eb248048af418ff562d0e49
Source dataset
uspto-grants-1997_05
Patent number
US05633281

Reaction notes

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