L-Lysine → HCID 67183043, compound

HRID 2064104Notes

Reaction equation

HRID 2064104 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].[NH2:34][C@H:35]([C:41]([OH:43])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40]>O>[NH2:34][C@H:35]([C:41]([OH:43])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40].[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

4

Reactant 2

HCID 5962L-LysineHCID 24763648HCID 24763648, compound

Product 1

HCID 67183043HCID 67183043, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
27.5 °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 methanol (50 ml) at 25-30° C., under argon, was added L-lysine (1.66 g, 0.010 mol). The reaction mixture was stirred at 25-30° C. for 0.5 h. Water (5 ml) was added to the reaction mixture and stirring continued further for 3 h at 25-30° 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, 92% yield. Aqueous solubility at pH 7 was >200 mg/ml.

Workup

  1. stirringstirring
  2. waitcontinued further for 3 h at 25-30° 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-02aa4fb357794eb7a25cd23933a58d85
Source dataset
uspto-grants-2012_10
Patent number
US08288416B2

Reaction notes

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