2-Hydrazinoethanol → HCID 69983113, compound

HRID 1167460Notes

Reaction equation

HRID 1167460 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1.[OH:28][CH2:29][CH2:30][NH:31][NH2:32]>CO.ClCCl>[OH:28][CH2:29][CH2:30][NH:31][N:32]=[C:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 80172-HydrazinoethanolHCID 69979965HCID 69979965, compound

Product 1

HCID 69983113HCID 69983113, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-(4-(4-Oxopiperidin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (125 mg, 0.33 mmol) was dissolved in MeOH (5 ml) and dichloromethane (5 ml), 2-hydroxyethylhydrazine (29 mg, 0.37 mmol) added, and the mixture stirred at ambient temperature under nitrogen for 18 hours. The mixture was evaporated, and the residue purified by chromatography on a 5 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 1.5% MeOH in dichloromethane. Relevant fractions were combined to give the desired product (98 mg). MS (ESP): 434 (MH+) for C20H24FN5O5.

Workup

  1. customThe mixture was evaporated
  2. customthe residue purified by chromatography on a 5 g silica Mega Bond Elut® column
  3. washeluting with a gradient
  4. temperatureincreasing in polarity from 0 to 1.5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-d217ad6718584c71b32870a947356c30
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

Loading…