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 1582349Notes

Reaction equation

HRID 1582349 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 80.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(4-(3(S)-Acetoxyacetamidopyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(3-isoxazolylaminomethyl)oxazolidin-2-one (105 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 ). NMR (DMSO-d6) δ: 1.83 (hextet, 1H); 2.14 (hextet, 1H); 3.20 (m, 1H); 3.29 (m overlapped by H2O, ˜1H); 3.42 (t overlapping m, 3H); 3.49 (m, 1H); 3.75 (dd, 1H); 3.82 (s, 2H); 4.07 (t, 1H); 4.37 (m, 1H); 4.83 (m, 1H); 5.37 (br, 1H); 6.00 (d, 1H); 6.51 (t, 1H); 6.75 (t, 1H); 7.10 (dd, 1H); 7.41 (dd, 1H); 7.85 (d, 1H); 8.37 (d, 1H). MS (ESP): 420 (MH+) for C19H22FN5O5

Workup

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

Sources & evidence

ORD record
ord-2d4a3d18f7954dd18696886ee806d5bb
Source dataset
uspto-grants-2004_05
Patent number
US06734200B1

Reaction notes

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