Hydroxyamine hydrochloride → HCID 88397677, compound

HRID 1728774Notes

Reaction equation

HRID 1728774 reaction equation
[C:1]([NH:4][CH:5]([C:16](=O)[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2].Cl.[NH2:35][OH:36].C([O-])(=O)C.[Na+]>CO>[C:1]([NH:4][CH:5]([C:16](=[N:35][OH:36])[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:27])([F:26])[F:28])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19016558HCID 19016558, compound

Product 1

HCID 88397677HCID 88397677, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of Example 4 (0.5 g) was dissolved in methanol followed by hydroxylamine hydrochloride (0.220 g) and sodium acetate (0.7 g). The reaction was stirred for 16 hours, the solvent was removed and the residue was dissolved in ethyl acetate (100 ml), washed with water (100 ml), dried (MgSO4), filtered and evaporated to yield an oil which was purified by chromatography on silica using dichloromethane/Et2O (3:1) to yield the title compound isomer A as a white solid, mp=200°-201° C.; found: C, 54.79; H, 4.24; N, 5.19; C23H20F6N2O2S requires C, 54.98; H, 4.01; N, 5.58%. Further elution yielded the title compound isomer B as a white solid, mp=200°-203° C.; found: C, 55.13; H, 4.14; N, 5.45; C23H20F6N2O2S requires C, 54.98; H, 4.01; N, 5.58 %.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto yield an oil which
  8. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-471fb1a638014483960b7a9d2448e187
Source dataset
uspto-grants-1994_07
Patent number
US05328927

Reaction notes

Loading…