Phosphoric Acid → HCID 86589931, compound

HRID 458738Notes

Reaction equation

HRID 458738 reaction equation
Cl.[F:2][C:3]1([F:29])[CH2:7][CH2:6][C@@H:5]([C@@:8]([OH:28])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]([O:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH:20]=[NH:21])[CH2:16][CH2:15]2)=[O:10])[CH2:4]1.[Na].[P:31](=[O:35])([OH:34])([OH:33])[OH:32]>O>[P:31]([OH:35])([OH:34])([OH:33])=[O:32].[F:29][C:3]1([F:2])[CH2:7][CH2:6][C@@H:5]([C@@:8]([OH:28])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:9]([O:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH:20]=[NH:21])[CH2:18][CH2:19]2)=[O:10])[CH2:4]1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 5360545SodiumHCID 86589930HCID 86589930, compound

Product 1

HCID 86589931HCID 86589931, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 7.0 g of 2-(1-(iminomethyl)piperidin-4-yl)ethyl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate monohydrochloride in 50 ml of ultrapure water was developed on reversed phase medium pressure liquid chromatography [ODS-AQ 120-S50 (YMC Co.)], and 300 ml of 1.0 M aqueous sodium dihydrogenephosphate solution, 300 ml of 0.2 M phosphoric acid and 300 ml of ultrapure water were flowed by the order stated, followed by elution with tetrahydrofuran/water=1/9. Distilling the solvent off under reduced pressure, the residue was crystallized in ethanol and recovered by filtration, to provide 6.5 g of the title compound as a colorless solid.

Workup

  1. washfollowed by elution with tetrahydrofuran/water=1/9
  2. distillationDistilling the solvent off under reduced pressure
  3. customthe residue was crystallized in ethanol
  4. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-8d658b93ffc743c9b2f63a48598d0243
Source dataset
uspto-grants-2007_03
Patent number
US07192969B2

Reaction notes

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