Benzaldehyde → HCID 53724959, compound

HRID 465667Notes

Reaction equation

HRID 465667 reaction equation
[NH2:1][C@@H:2]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)[C:3]([NH:5][C:6]1[C:11](F)=[CH:10][C:9](F)=[CH:8][C:7]=1F)=[O:4].[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH4-].[Na+].OO>C1(C)C=CC=CC=1.C(OCC)(=O)C.CO.O>[CH3:3][CH:2]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH:6]([CH3:11])[CH3:7])[C:6]=1[NH:5][C:3](=[O:4])[C@@H:2]([NH:1][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)[CH3:15]

Participants

9

Reactant 4

HCID 240BenzaldehydeHCID 784Hydrogen PeroxideHCID 4311764Sodium borohydrideHCID 54132018HCID 54132018, compound

Product 1

HCID 53724959HCID 53724959, compoundYield 18.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (S)-α-amino-4-(phenylmethoxy)-N-(2,4,6-trifluorophenyl)benzenepropanamide (1.0 g, 2.3 mmol) and benzaldehyde (0.25 g, 2.3 mmol) in toluene was heated under reflux with the azeotropic removal of water (1 hr). The resulting solution was cooled (25° C.), then methanol (30 mL) and an excess of sodium borohydride was added, and the resulting slurry was stirred (2h, 25° C.). To the resulting mixture was added 3% aqueous H2O2 (ca. 10 mL), and the resulting mixture was again stirred (1 hr, 25° C.). The resulting mixture was diluted with ethyl acetate (200 mL), washed with water (2×100 mL), washed with brine (1×100 mL), then dried (MgSO4) and concentrated. The resulting oil was triturated with ether:hexane (1:1) and the resulting precipitate was collected by filtration to yield 0.11 g (9.1%) of the title compound, mp 127°-129° C.

Workup

  1. washwashed with water (2×100 mL)
  2. washwashed with brine (1×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting oil was triturated with ether:hexane (1:1)
  6. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-194a8de7e8d14f2aba2f3e466cdd34ab
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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