Sodium Hydroxide → HCID 66621883, compound

HRID 415993Notes

Reaction equation

HRID 415993 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][C@@H:19]3[CH2:23][CH2:22][N:21]([CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:20]3=[O:30])=[C:13]([Cl:31])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[Cl:17][C:15]1[CH:16]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH:12]=[C:13]([Cl:31])[C:14]=1[CH2:18][C@@H:19]1[CH2:23][CH2:22][N:21]([CH:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[C:20]1=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 666221203',5'-dichloro-4'-[(R)-2-oxo-1-(tetrahydro-pyran-4-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 66621883HCID 66621883, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a solution of 3′,5′-dichloro-4′-[(R)-2-oxo-1-(tetrahydro-pyran-4-yl)-pyrrolidin-3-ylmethyl]-biphenyl-4-carboxylic acid methyl ester (2.56 g, 5.5 mmol) in methanol (25 mL) with 5N aqueous sodium hydroxide (5.5 mL). Heat the reaction to 60° C. and stir for 1 hr. Cool to room temperature, quench with 1N hydrochloric acid and extract the aqueous with ethyl acetate. Wash the organic layer with brine, dry over magnesium sulfate, and filter. Remove the solvent under vacuum to afford 2.48 g (100%) of desired product: MS (m/z): 448 (M+).

Workup

  1. temperatureHeat
  2. customthe reaction to 60° C.
  3. customquench with 1N hydrochloric acid
  4. extractionextract the aqueous with ethyl acetate
  5. washWash the organic layer with brine
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. customRemove the solvent under vacuum

Sources & evidence

ORD record
ord-b3ccfb779cdf4b29ae2b19be9cfa34d2
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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