Sulfuric Acid → HCID 178474859, compound

HRID 2274750Notes

Reaction equation

HRID 2274750 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.[S:33](=[O:37])(=[O:36])([OH:35])[OH:34].C(O)(C)C>CO>[S:33]([OH:37])([OH:36])(=[O: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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 178474856HCID 178474856, compound

Product 1

HCID 178474859HCID 178474859, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

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 (50.5 mg, 0.115 mmol) in methanol (1.2 mL) was added 0.5 M sulfuric acid in isopropanol (0.64 mL, 0.32 mmol) and the resulting mixture heated to 55° C. to give an almost clear solution. The resulting mixture was cooled to room temperature and stirred for an additional 2 h. The resulting solid was filtered, washed with methyl tert-butyl ether (0.5 mL) and dried under reduced pressure at 50° C. to afford the title compound (48 mg, 77.7%) as a crystalline solid which was characterized by XRPD. FIG. 6 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 monosulfate. Characteristic peaks, expressed in degrees 2θ, are listed in Table 4.

Workup

  1. customto give an almost clear solution
  2. temperatureThe resulting mixture was cooled to room temperature
  3. filtrationThe resulting solid was filtered
  4. washwashed with methyl tert-butyl ether (0.5 mL)
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-1b52a684e4c94f538a1a8a377ed1eee9
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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