Phosphoric Acid → HCID 178474858, compound

HRID 2274748Notes

Reaction equation

HRID 2274748 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])[CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH2:27][C:28]2[NH:32][N:31]=[N:30][CH:29]=2)=[CH:21][CH:20]=1.[P:33](=[O:37])([OH:36])([OH:35])[OH:34].C(O)(C)C>C(O)C.ClCCl>[P:33]([OH:37])([OH:36])([OH:35])=[O:34].[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[O:10][C:9]2=[O:18])[CH:5]=[CH:4][C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH2:27][C:28]2[NH:32][N:31]=[N:30][CH:29]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 3776IsopropanolHCID 178474856HCID 178474856, compound

Product 1

HCID 178474858HCID 178474858, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide (50.69 mg, 0.116 mmol) in ethanol (1.0 mL) and dichloromethane (0.6 mL) was added 0.5 M phosphoric acid in isopropanol (0.6 mL, 0.30 mmol), and the resulting mixture stirred at room temperature for 10 min. The solvent volume was reduced to about 0.7 mL, ethanol (0.9 mL) was added, and the resulting mixture was refluxed for 20 min. The mixture was cooled to room temperature and stirred for an additional 2 h. The resulting solid was filtered, washed with methyl tert-butyl ether (0.6 mL) and dried under reduced pressure at 50° C. to afford the title compound (69.1 mg, 94.2%) as a crystalline solid which was characterized by XRPD. FIG. 4 shows a characteristic X-ray powder diffraction (XRPD) pattern of crystalline N-{[(5S)-3-(2-fluoro-4′-{[(1H-1,2,3-triazol-5-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide monophosphate. Characteristic peaks, expressed in degrees 2θ, are listed in Table 3.

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was refluxed for 20 min
  3. temperatureThe mixture was cooled to room temperature
  4. stirringstirred for an additional 2 h
  5. filtrationThe resulting solid was filtered
  6. washwashed with methyl tert-butyl ether (0.6 mL)
  7. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-f2ba439fee314beaafce9617ecfac9c2
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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