Methanol → HCID 68545756, compound

HRID 1446070Notes

Reaction equation

HRID 1446070 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:28][CH:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:5]=[CH:6][C:7]=1[C:8]([CH2:10][O:11][CH:12]1[CH2:17][O:16][C:15]2=[N:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][N:14]2[CH2:13]1)=C.C[OH:36]>O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]([N:24]2[CH2:28][CH:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]2=[O:34])[CH:5]=[CH:6][C:7]=1[C:8](=[O:36])[CH2:10][O:11][CH:12]1[CH2:17][O:16][C:15]2=[N:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][N:14]2[CH2:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 68542969HCID 68542969, compound

Product 1

HCID 68545756HCID 68545756, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

N-(3-{3-Fluoro-4-[1-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-vinyl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide (48 mg) was dissolved in 1.5 mL methanol, followed by addition of NaIO4 (54 mg) and OsO4 (0.02 mL, 2.5% in water). The solution was stirred at room temperature for 4 hours and then Celite (500 mg) was added. The resulting mixture was stirred for 30 min before it was filtered and washed with EtOAc. The organic layer was dried over Na2SO4 and purified with preparative TLC (CH2Cl2/MeOH, v/v, 10/1). The titled compound was obtained as yellow solid (8 mg). ESI MS m/z 478 (M+H). 1H NMR (400 MHz, MeCN-d3) 8.06 (t, J=8.4 Hz, 1H), 7.74 (s, 1H), 7.69 (dd, J=14.0, 2.0 Hz, 1H), 7.52 (dd, J=8.8, 2.4 Hz, 1H), 6.84 (b, 1H), 4.95-5.00 (m, 2H), 4.83-4.92 (m, 1H), 4.78 (dt, J=12.0, 2.8 Hz, 1H), 4.53 (d, J=12.8 Hz, 1H), 4.41 (dt, J=12.8, 2.0 Hz, 1H), 4.30-4.35 (m, 1H), 4.29 (dd, J=12.8, 3.2 Hz, 1H), 4.21 (t, J=9.2 Hz, 1H), 3.89 (dd, J=9.2, 6.4 Hz, 1H), 3.58-3.68 (m, 2H), 3.39 (d, J=5.2 Hz, 1H), 1.98 (s, 3H).

Workup

  1. additionCelite (500 mg) was added
  2. stirringThe resulting mixture was stirred for 30 min before it
  3. filtrationwas filtered
  4. washwashed with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. custompurified with preparative TLC (CH2Cl2/MeOH, v/v, 10/1)

Sources & evidence

ORD record
ord-14b77f30222a44cb9b5f3edeb97db5ac
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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