Sulfuric Acid → HCID 178474859, compound

HRID 2274751Notes

Reaction equation

HRID 2274751 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH: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[N:29]=[N:30][NH:31][CH:32]=2)=[CH:21][CH:20]=1.[S:33](=[O:37])(=[O:36])([OH:35])[OH:34].C(O)(C)C>C(O)(C)C.O>[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:29][N:30]=[N:31][CH:32]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 178474584HCID 178474584, compound

Product 1

HCID 178474859HCID 178474859, compound

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

To a stirred suspension of N-[3-(2-Fluoro-4′-{[(1H-[1,2,3]triazol-4-ylmethyl)-amino]-methyl}-biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide (49 mg, 0.11 mmol) in 4:1 isopropanol/water (0.8 mL) was added dropwise 0.5 M sulfuric acid in isopropanol (0.65 mL, 0.33 mmol). The mixture was then stirred for 2 h and the solvent removed under reduced pressure to give the title compound as an amorphous off-white solid which was characterized by XRPD. FIG. 7 shows a characteristic X-ray powder diffraction (XRPD) pattern of amorphous 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.

Workup

  1. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6d4833f00561488ca31b37c06e738668
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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