Hydroxyamine hydrochloride → HCID 86744343, compound

HRID 1073712Notes

Reaction equation

HRID 1073712 reaction equation
[C:1]([CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][CH:7]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:6]1=[O:34])(=O)[CH3:2].Cl.[NH2:36][OH:37]>C(O)C.C(OC(C)C)(C)C>[OH:37][N:36]=[C:1]([CH3:2])[CH2:4][N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:8][CH:7]([NH:22][C:23]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[C:6]1=[O:34]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 20097487HCID 20097487, compound

Product 1

HCID 86744343HCID 86744343, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of (3RS)-1-acetylmethyl-1,3-dihydro-3-(2- indolylcarbonylamino) -5-phenyl-2H-1,4-benzodiazepine-2-one (0.42 g), hydroxylamine hydrochloride (62.5 mg) in ethanol (20 ml) was stirred at room temperature for 40 hours. The mixture was evaporated to dryness and the residue was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (40:1). The fractions containing the objective product were combined and evaporated to give a pale green oil, which was pulverized in diisopropyl ether to afford (3RS)-1-(2-hydroxyiminopropyl)-1,3-dihydro-3-(2-indolylcarbonylamino) -5-phenyl-2H-1,4-benzodiazepine-2-one (177 mg).

Workup

  1. customThe mixture was evaporated to dryness
  2. additionthe residue was subjected to column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (40:1)
  3. additionThe fractions containing the objective product
  4. customevaporated
  5. customto give a pale green oil, which

Sources & evidence

ORD record
ord-73ef4c091d39459b98f51071371cceda
Source dataset
uspto-grants-1990_11
Patent number
US04970207

Reaction notes

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