Trifluoroacetic acid methylene chloride → HCID 68545922, compound

HRID 1446094Notes

Reaction equation

HRID 1446094 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:27]2[CH2:31][CH:30]([CH2:32][O:33][P:34](=[O:45])([O:40]C(C)(C)C)[O:35]C(C)(C)C)[O:29][C:28]2=[O:46])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([O:14][CH:15]2[CH2:20][O:19][C:18]3=[N:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][N:17]3[CH2:16]2)=[CH:12][CH:13]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[F:1][C:2]1[CH:3]=[C:4]([N:27]2[CH2:31][CH:30]([CH2:32][O:33][P:34](=[O:35])([OH:45])[OH:40])[O:29][C:28]2=[O:46])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[N:10][C:11]([O:14][CH:15]2[CH2:20][O:19][C:18]3=[N:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][N:17]3[CH2:16]2)=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68550409HCID 68550409, compound

Product 1

HCID 68545922HCID 68545922, compoundYield 74.1%

Procedure

Phosphoric acid mono-(3-{3-fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl) ester was prepared according to the scheme shown in FIG. 17. Phosphoric acid di-tert-butyl ester 3-{3-fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester (13 mg) was dissolved with 1 mL TFA/CH2Cl2 (v/v, ½). The resulting solution was stirred at room temperature for 1 hour before all the solvent was removed. The residue was washed with 3 mL CH2Cl2, 3 mL EtOAc and 3 mL MeOH consequently. The residue was dried in vacuo to give the titled compound (8 mg) as white solid. ESI MS m/z 552 (M+H).

Workup

  1. customPhosphoric acid mono-(3-{3-fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl) ester was prepared
  2. customwas removed
  3. washThe residue was washed with 3 mL CH2Cl2, 3 mL EtOAc and 3 mL MeOH consequently
  4. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-dd3462884dcb40d4a5c078e0af0cf26c
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

Loading…