Phosphoric Acid → HCID 178474858, compound

HRID 2274749Notes

Reaction equation

HRID 2274749 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].O1CCCC1>C(O)(C)C>[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

5

Reactant 3

HCID 1004Phosphoric AcidHCID 8028TetrahydrofuranHCID 178474856HCID 178474856, compound

Product 1

HCID 178474858HCID 178474858, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

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 isopropanol (1.0 mL) was added 0.5 M phosphoric acid in isopropanol (0.7 mL, 0.35 mmol), and the resulting mixture stirred at room temperature for 20 min. The resulting stirred suspension was heated to 80° C. and then concentrated under reduced pressure to give a solid. The solid was treated with aqueous tetrahydrofuran, stirred, and concentrated under reduced pressure to give the title compound as an amorphous solid which was characterized by XRPD. FIG. 5 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 monophosphate.

Workup

  1. stirringThe resulting stirred suspension
  2. temperaturewas heated to 80° C.
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid
  5. stirringstirred
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-477fc1e798c74874a2655673fd5d7aff
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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