Ammonia → HCID 21529368, compound

HRID 1658436Notes

Reaction equation

HRID 1658436 reaction equation
C([O:4][CH2:5][CH:6]([OH:30])[CH:7]([OH:29])[CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])=[N:12][CH2:11][C:10]1=[O:28])(=O)C.N>CO>[Cl:20][C:18]1[CH:17]=[CH:16][C:15]2[N:9]([CH2:8][CH:7]([OH:29])[CH:6]([OH:30])[CH2:5][OH:4])[C:10](=[O:28])[CH2:11][N:12]=[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:14]=2[CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21529367HCID 21529367, compound

Product 1

HCID 21529368HCID 21529368, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14 g of 1-(4-acetoxy-2,3-dihydroxybutyl)-7-chloro-5-(2-fluorophenyl)-1, 3-dihydro-2H-1,4-benzodiazepin-2-one are dissolved in 30 ml of methanol, treated with 15 ml of 25% aqueous ammonia and stirred at room temperature for 16 hours. The mixture is then evaporated to dryness and chromatographed on silica gel with ethyl acetate/methanol (9:1 ). The pure fractions are combined and evaporated. There is obtained 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-1-(2,3,4-trihydroxybutyl)-2H-1,4-benzodiazepin-2-one in the form of a foam.

Workup

  1. customThe mixture is then evaporated to dryness
  2. customchromatographed on silica gel with ethyl acetate/methanol (9:1 )
  3. customevaporated

Sources & evidence

ORD record
ord-7c4df427e6bd459fa4416b4e3afb0f42
Source dataset
uspto-grants-1976_06
Patent number
US03963777

Reaction notes

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