Hydrochloric Acid → HCID 178474857, compound

HRID 2274745Notes

Reaction equation

HRID 2274745 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.[ClH:33]>CO.C(OCC)(=O)C.O1CCOCC1>[ClH:33].[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 2

HCID 313Hydrochloric AcidHCID 178474856HCID 178474856, compound

Product 1

HCID 178474857HCID 178474857, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

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 (3.5 g, 7.75 mmol) in methanol (4 mL) and ethyl acetate (17.5 mL) was added 4.0 N hydrogen chloride in dioxane (8.0 mL). The resulting mixture was stirred for 8 h, the solvent removed under reduced pressure and the residue dried in vacuo. The residue was suspended in 10% methanol in acetonitrile (17.5 mL) and stirred at room temperature for 1 h. The solid was filtered, washed with 10% methanol in acetonitrile (17.5 mL) and dried under reduced pressure at 45° C. to afford the title compound (3.32 g, 90.2%) as a crystalline solid which was characterized by XRPD. FIG. 1 shows a characteristic X-ray powder diffraction (XRPD) pattern 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 monohydrochloride. Characteristic peaks, expressed in degrees 2θ, are listed in Table 1.

Workup

  1. customthe solvent removed under reduced pressure
  2. customthe residue dried in vacuo
  3. stirringstirred at room temperature for 1 h
  4. filtrationThe solid was filtered
  5. washwashed with 10% methanol in acetonitrile (17.5 mL)
  6. customdried under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-22a5b7a16aff4dd6b1d36c3a465aeaa5
Source dataset
uspto-grants-2015_09
Patent number
US09126991B2

Reaction notes

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