HCID 86613448, compound → HCID 67279585, compound

HRID 1893863Notes

Reaction equation

HRID 1893863 reaction equation
[CH2:1]([O:8][C:9](=[O:48])[CH2:10][CH2:11][C:12]([O:14][C:15]1([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH2:40][C@H:39]([CH2:41][NH:42][C:43](=[O:45])[CH3:44])[O:38][C:37]3=[O:46])=[CH:32][C:31]=2[F:47])[CH2:20][CH2:19][N:18](OC(C)(C)C)[C:17](=C=O)[CH2:16]1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9](=[O:48])[CH2:10][CH2:11][C:12]([O:14][C:15]1([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH2:40][C@H:39]([CH2:41][NH:42][C:43](=[O:45])[CH3:44])[O:38][C:37]3=[O:46])=[CH:32][C:31]=2[F:47])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86613448HCID 86613448, compound

Product 1

HCID 67279585HCID 67279585, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

820 mg of succinic acid 4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-1-tert-butoxy-carbonyl-piperidin-4-yl ester benzyl ester (MW: 671.72, 1.23 mmol) were dissolved in 4 ml of trifluoro acetic acid. The reaction mixture was stirred at room temperature for one hour. The solvent was evaporated, the residue dissolved in 30 ml of a 9/1 dichloromethane/methanol mixture and the organic layer washed successively with 30 ml of a saturated aqueous sodium bicarbonate solution and 30 ml of brine. The organic layer was dried over magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue was purified by chromatography over silica, using a 95/5 dichloromethane/methanol mixture with 2% triethylamine as eluent. Yield: 420 mg, 60%. MS: 572.7 (M+H)+, Method ESI+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in 30 ml of a 9/1 dichloromethane/methanol mixture
  3. washthe organic layer washed successively with 30 ml of a saturated aqueous sodium bicarbonate solution and 30 ml of brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customThe residue was purified by chromatography over silica

Sources & evidence

ORD record
ord-81dc2b6bb8114b7aa552bb09c33e8aa1
Source dataset
uspto-grants-2013_08
Patent number
US08513231B2

Reaction notes

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