Hydroxyamine hydrochloride → HCID 86759171, compound

HRID 1167479Notes

Reaction equation

HRID 1167479 reaction equation
O=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][O:19][C:20]4[CH:24]=[CH:23][O:22][N:21]=4)[O:15][C:14]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3]1.Cl.[NH2:28][OH:29].C([O-])(=O)C.[Na+]>ClCCl.CO.O>[N:28](=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][O:19][C:20]4[CH:24]=[CH:23][O:22][N:21]=4)[O:15][C:14]3=[O:25])=[CH:9][C:8]=2[F:26])[CH2:3]1)[OH:29]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 69982214HCID 69982214, compound

Product 1

HCID 86759171HCID 86759171, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(4-(3-Oxo-1-pyrrolidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (124 mg, 0.34 mmol) was dissolved in a mixture of dichloromethane (10 ml) and MeOH (10 ml), and treated with a solution of hydroxylamine hydrochloride (220 mg, 3.17 mmol) and sodium acetate (500 mg) in water (2 ml). After stirring at ambient temperature for 4 hours, solvents were evaporated, and the residue triturated with water (10 ml), solid filtered and dried to give the desired product (118 mg) as a single isomer of unknown geometry. MS (ESP): 377 (MH+) for C17H17FN4O5.

Workup

  1. customsolvents were evaporated
  2. customthe residue triturated with water (10 ml), solid
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-5543f14ceef2438692941d2277ee39cf
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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