Hydroxyamine hydrochloride → HCID 86744343, compound

HRID 258095Notes

Reaction equation

HRID 258095 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-4e675712e3eb483d968bf9741e41e28a
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

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