Methanol → HCID 24969354, compound

HRID 1940192Notes

Reaction equation

HRID 1940192 reaction equation
CO.O.[BH4-].[Na+].ClCCl.[CH2:9]([N:13]1[C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[N:16][C@H:15]([CH2:32][C:33]([OH:35])=[O:34])[C:14]1=[O:36])[CH:10]([CH3:12])[CH3:11]>>[CH2:9]([N:13]1[C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[C@@H:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[NH:16][C@H:15]([CH2:32][C:33]([OH:35])=[O:34])[C:14]1=[O:36])[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 5

HCID 887MethanolHCID 962Water2×HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 22880261HCID 22880261, compound

Product 1

HCID 24969354HCID 24969354, compoundYield 56.4%

Procedure

In a mixture solvent (methanol:water=6:1) (0.7 ml) was dissolved (3R)-1-isobutyl-7-chloro-5-(2-chlorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepine-3-acetic acid (30 mg) obtained in Example 13. To the solution was added sodium borohydride (10 mg). The reaction mixture was stirred for two hours at room temperature, to which were added dichloromethane (50 ml) and water (50 ml). The aqueous layer was made acid, then the organic layer was washed with a saturated aqueous saline solution, followed by drying over anhydrous sodium sulfate. The solvent was removed, and the residue was recrystallized from dichloromethane/petroleum ether to give 17 mg of colorless crystals, m.p. 184°-188° C.

Workup

  1. washthe organic layer was washed with a saturated aqueous saline solution
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customThe solvent was removed
  4. customthe residue was recrystallized from dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-698611701f024989816605cd847e4dea
Source dataset
uspto-grants-1997_12
Patent number
US05698691

Reaction notes

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