Methyl carbazate → HCID 69982559, compound

HRID 1167459Notes

Reaction equation

HRID 1167459 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.[C:28]([O:32][CH3:33])(=[O:31])[NH:29][NH2:30]>CO.ClCCl>[CH3:33][O:32][C:28]([NH:29][N:30]=[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)=[O:31]

Participants

5

Reactant 2

HCID 80519Methyl carbazateHCID 69979965HCID 69979965, compound

Product 1

HCID 69982559HCID 69982559, compoundYield 66.4%

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), methyl carbazate (34 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% MeOH in dichloromethane. Relevant fractions were combined to give the desired product (98 mg).

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% MeOH in dichloromethane

Sources & evidence

ORD record
ord-eb6d5c65b6de43f297d7029106379fa1
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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