Sodium Hydroxide → HCID 24852104, compound

HRID 1670839Notes

Reaction equation

HRID 1670839 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][N:19]3[CH2:23][CH2:22][CH:21]([CH:24]4[CH2:29][CH2:28][CH2:27][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+]>C1COCC1>[Cl:31][C:13]1[CH:12]=[C:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)[CH:16]=[C:15]([Cl:17])[C:14]=1[CH2:18][N:19]1[CH2:23][CH2:22][CH:21]([CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[C:20]1=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57658001HCID 57658001, compound

Product 1

HCID 24852104HCID 24852104, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Treat a solution of 3′,5′-dichloro-4′-(3-cyclohexyl-2-oxo-pyrrolidin-1-ylmethyl)-biphenyl-4-carboxylic acid methyl ester (0.6 g) in THF (15 mL) with 5N NaOH (5 mL) and stir at 50° C. for 12 hours. Quench the reaction with HCl (1N, 25 mL). Partition the mixture between ethyl acetate and water. Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford 0.56 g (96%) of the title compound. MS (m/z): 446 (M+).

Workup

  1. customQuench
  2. customthe reaction with HCl (1N, 25 mL)
  3. customPartition the mixture between ethyl acetate and water
  4. dry with materialDry the organic layer (Na2SO4)
  5. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-d5ca21cfeffc414bafe762c59a3f964f
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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