Hydrochloric Acid → HCID 178448522, compound

HRID 1625035Notes

Reaction equation

HRID 1625035 reaction equation
[OH-].[Li+].[F:3][C:4]1[C:5]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C@H:32]3[CH2:37][CH2:36][C@H:35]([O:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][O:40]4)[CH2:34][CH2:33]3)=[CH:26][CH:25]=2)=[CH:6][C:7](=[O:23])[N:8]([CH2:10][CH2:11][C@@:12]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([O:15]CC)=[O:14])[CH:9]=1.Cl>C(O)C>[F:3][C:4]1[C:5]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C@H:32]3[CH2:33][CH2:34][C@H:35]([O:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][O:40]4)[CH2:36][CH2:37]3)=[CH:26][CH:25]=2)=[CH:6][C:7](=[O:23])[N:8]([CH2:10][CH2:11][C@@:12]([CH3:22])([S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([OH:15])=[O:14])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178471465HCID 178471465, compound

Product 1

HCID 178448522HCID 178448522, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Aqueous lithium hydroxide (2.0 M, 5.8 mL, 2.3 mmol) was added to a solution of ethyl (2R)-4-[5-fluoro-2-oxo-4-(4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}-phenyl)pyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoate (1.4 g, 2.3 mmol) in ethanol (40 mL). The reaction was heated to 50° C. for 3 h. The reaction was allowed to cool to ambient temperature and then acidified to a pH of ˜3 with 1.0 N aq. HCl. The mixture was extracted with EtOAc (3×150 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure to afford the title compound as a white solid (1.28 g, 98%). MS (LCMS) m/z 580.3 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe mixture was extracted with EtOAc (3×150 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-53d891bcdf464c8ba44597424dcf19c8
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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