Sodium hydride → HCID 22873045, compound

HRID 1781956Notes

Reaction equation

HRID 1781956 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:27][C:28]([F:42])([F:41])[C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:32]Br>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][O:11][CH2:32][C:31]1[CH:34]=[C:35]([C:37]([F:39])([F:40])[F:38])[CH:36]=[C:29]([C:28]([F:27])([F:41])[F:42])[CH:30]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 16213633(S)-tert-Butyl (3-hydroxy-1,1-diphenylpropan-2-yl)carbamate

Product 1

HCID 22873045HCID 22873045, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° C.) of (S)-2-t-butoxycarbonylamino-3,3-diphenylpropan-1-ol (2.04 g, 6.2 mmol, Example 1 g) in tetrahydrofuran (50 ml) and dimethylformamide (10 ml) was added sodium hydride (0.187 g, 80% suspension in oil) over 15 minutes. After an additional 10 minutes 3,5-bis(trifluoromethyl)benzyl bromide (1.14 ml) was added and the solution stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue partitioned between CH2Cl2 and water. After washing the organic phase with saturated brine and drying (MgSO4), the solvent was removed in vacuo and the residue chromatographed on silica gel in ethyl acetate/hexane (0:100 to 50:50) to give (S)-2-t-butoxycarbonylamino-1-((3.5bis(trifluoromethyl)phenyl)methyloxy)3,3-diphenylpropane, 2.92 g.

Workup

  1. customover 15 minutes
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between CH2Cl2 and water
  4. washAfter washing the organic phase with saturated brine
  5. dry with materialdrying (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customthe residue chromatographed on silica gel in ethyl acetate/hexane (0:100 to 50:50)

Sources & evidence

ORD record
ord-3592964bb411464a9d252afbb2f06a56
Source dataset
uspto-grants-1997_05
Patent number
US05633281

Reaction notes

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