Methanol → HCID 67695525, compound

HRID 1489525Notes

Reaction equation

HRID 1489525 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][C:13]([NH:15][CH:16]1[N:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=2[N:18]2[CH2:33][C@H:34]([C:36](OC)=[O:37])[N:35]=[C:17]12)=[O:14].CO.O>C1COCC1>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][C:13]([NH:15][CH:16]1[N:22]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=2[N:18]2[CH2:33][C@H:34]([CH2:36][OH:37])[N:35]=[C:17]12)=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 86751417HCID 86751417, compound

Product 1

HCID 67695525HCID 67695525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (6.5 mg, 0.3 mmol) was added to a solution of (2R)-3-(2,4-dichlorophenyl)-N-{1,2-dihydro-2-methoxycarbonyl-6-phenyl-4H-imidazo [1,2-a][1,4]benzodiazepin-4-yl}propanamide (160 mg, 0.3 mmol) in THF (20 mL) and the mixture was stirred at room temperature for 18 h. The mixture was cooled to 0° C. and methanol then water were added. The solvent was evaporated under reduced pressure, ethyl acetate was added and the mixture was washed with brine, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH (97.5:2.5) to give (2R)-3-(2,4-dichlorophenyl)-N-{1,2-dihydro-2-hydroxymethyl-6-phenyl-4H-imidazo[1,2-a][1,4]benzodiazepin-4-yl}propanamide as a foam.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customThe solvent was evaporated under reduced pressure, ethyl acetate
  3. additionwas added
  4. washthe mixture was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with CH2Cl2 /MeOH (97.5:2.5)

Sources & evidence

ORD record
ord-d11c7558418d4e4da75bd99190ea6ea9
Source dataset
uspto-grants-1997_10
Patent number
US05679672

Reaction notes

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