Hydroxylamine → HCID 86755439, compound

HRID 1420630Notes

Reaction equation

HRID 1420630 reaction equation
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:6]([C:25](O)=[O:26])[CH2:5]1)(=[O:3])[CH3:2].[OH:28][N:29]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.NO>CN(C)C=O.O.C(OCC)(=O)C.CO>[OH:28][NH:29][C:25]([CH:6]1[N:7]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([C:1](=[O:3])[CH3:2])[CH2:5]1)=[O:26]

Participants

9

Reactant 4

HCID 787HydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18782060HCID 18782060, compound

Product 1

HCID 86755439HCID 86755439, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a crude mixture of 1-acetyl-4-(4-hydroxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylic acid (0.55 g) and N-hydroxybenzotriazole (0.414 g) in 5 ml of N,N-dimethylformamide was added 0.684 g of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The mixture was stirred at room temperature for 1 hr and then 750 μL of hydroxylamine in water (50%) was added and the mixture stirred at room temperature overnight. The mixture was diluted with ethyl acetate and then washed with H2O, 2N citric acid, brine and dried (Na2SO4). The solvent was removed under vacuum to give a solid. Chromatography on silica gel with 10% methanol in ethyl acetate as solvent gave a solid which was dried at 78° C under vacuum overnight to give an off-white foam; Mass spectrum (ES) 406.1 (M+H); Anal. Calcd. For C18H19N3O6S; C, 53.3; H, 4.7; N, 10.4. Found: C, 52.6; H, 5.2; N, 10.4.

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. washwashed with H2O, 2N citric acid, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed under vacuum
  5. customto give a solid
  6. customwas dried at 78° C under vacuum overnight
  7. customto give an off-white foam

Sources & evidence

ORD record
ord-fe8e7316eb9c489d80b8fbd95aea09f6
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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