Benzaldehyde → HCID 131728519, compound

HRID 1172553Notes

Reaction equation

HRID 1172553 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:30])[C:13]2[O:19][C:18]3[C:20]([Cl:26])=[CH:21][C:22]([CH2:24][NH2:25])=[CH:23][C:17]=3[CH2:16][S:15](=[O:28])(=[O:27])[C:14]=2[CH:29]=1)=[O:9].[CH:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO.O>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:30])[C:13]2[O:19][C:18]3[C:20]([Cl:26])=[CH:21][C:22]([CH2:24][NH:25][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:27])(=[O:28])[C:14]=2[CH:29]=1)=[O:9]

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 131728517HCID 131728517, compound

Product 1

HCID 131728519HCID 131728519, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium acetate (0.107 g, 1.30 mmol) was added to a solution of Example 198k (0.2 g, 0.52 mmol) in dry methanol (15 mL). Subsequently benzaldehyde (0.083 mL, 0.78 mmol) was added and the reaction mixture was stirred for 2.5 h. It was then chilled and treated with sodium borohydride (0.19 g, 0.52 mmol). The reaction mixture was stirred overnight at room temperature, then treated with an aqueous 10% sodium bicarbonate solution (2 mL), diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.095 g, (38.46%); 1H NMR (DMSO-d6): δ 2.70 (s, 3H, CH3), 3.81 (s, 4H, 2CH2), 3.91 (s, 3H, OCH3), 4.71 (s, 2H, CH2), 7.26-7.34 (m, 5H, Ar), 7.51 (s, 1H, Ar), 8.09 (s, 2H, Ar), 8.46 (s, 1H, Ar); MS: m/e (EI+) 472 (M+1).

Workup

  1. temperatureIt was then chilled
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-7d017596a3db4593b1d1314b197b74d4
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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