Ethanol → HCID 178494754, compound

HRID 2064103Notes

Reaction equation

HRID 2064103 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]3[CH2:24][CH2:23][C:22]([O:28][P:29](=[O:32])([OH:31])[OH:30])([CH2:25][O:26][CH3:27])[CH2:21][CH2:20]3)=[C:14]([F:33])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].C(O)C.[NH2:37][C@H:38]([C:46]([OH:48])=[O:47])[CH2:39][CH2:40][CH2:41][NH:42][C:43](=[NH:45])[NH2:44]>O>[NH2:37][C@H:38]([C:46]([OH:48])=[O:47])[CH2:39][CH2:40][CH2:41][NH:42][C:43](=[NH:44])[NH2:45].[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([N:19]3[CH2:24][CH2:23][C:22]([O:28][P:29](=[O:30])([OH:31])[OH:32])([CH2:25][O:26][CH3:27])[CH2:21][CH2:20]3)=[C:14]([F:33])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 24763648HCID 24763648, compoundHCID 178418600HCID 178418600, compound

Product 1

HCID 178494754HCID 178494754, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82.5 °C

Procedure

To a solution of phosphoric acid mono-(1-{4-[(S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2,6-difluorophenyl}-4-methoxymethyl-piperidin-4-yl)ester (5.0 g, 0.010 mol anhydrous ethanol (50 ml) at 25-30° C., under argon, was added L-arginine (1.76 g, 0.010 mol). The reaction mixture was stirred at 80-85° C. for 0.5 h. Water (5 ml) was added to the reaction mixture and stirring continued further for 1 h at 80-85° C. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. Acetone (25 ml) was added to the residue and triturated. The solvent was decanted. This procedure was repeated twice with acetone (50 ml). Acetone after the third trituration was decanted and the residue dried under reduced pressure to obtain the product as off-white solid, 6.1 g, 91% yield. Aqueous solubility at pH 7 was >200 mg/ml.

Workup

  1. stirringstirring
  2. waitcontinued further for 1 h at 80-85° C
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate evaporated under reduced pressure
  5. additionAcetone (25 ml) was added to the residue
  6. customtriturated
  7. customThe solvent was decanted
  8. customAcetone after the third trituration was decanted
  9. customthe residue dried under reduced pressure

Sources & evidence

ORD record
ord-bc90fdc944934524955d1636af129569
Source dataset
uspto-grants-2012_10
Patent number
US08288416B2

Reaction notes

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