Potassium Carbonate → N-[(3S)-1-[2-fluoro-4-[(5S)-5-[(isoxazol-3-ylamino)methyl]-2-oxo-oxazolidin-3-yl]phenyl]pyrrolidin-3-yl]-2-hydroxy-acetamide

HRID 8166Notes

Reaction equation

HRID 8166 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27]4[CH:31]=[CH:30][O:29][N:28]=4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:10]1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27]4[CH:31]=[CH:30][O:29][N:28]=4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:10]1)=[O:7]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 695849643-(4-(3(S)-Acetoxyacetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(3-isoxazolylamino-methyl)oxazolidin-2-one

Product 1

HCID 497431N-[(3S)-1-[2-fluoro-4-[(5S)-5-[(isoxazol-3-ylamino)methyl]-2-oxo-oxazolidin-3-yl]phenyl]pyrrolidin-3-yl]-2-hydroxy-acetamideYield 8.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-(3(S)-Acetoxyacetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(3-isoxazolylamino-methyl)oxazolidin-2-one (1051 mg, 0.23 mM) and potassium carbonate (300 mg, 2.2 mM) were stirred at ambient temperature under nitrogen in methanol (20 ml) for 20 minutes. The mixture was evaporated to dryness and triturated with water (10 ml) to gave the desired product (77 mg).

Workup

  1. customThe mixture was evaporated to dryness
  2. customtriturated with water (10 ml)

Sources & evidence

ORD record
ord-4da7f0e9e12b4595a727327cc42d2122
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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