Water → HCID 66621869, compound

HRID 416001Notes

Reaction equation

HRID 416001 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=4)=[CH:15][C:14]=3[O:29][C:30]([F:33])([F:32])[F:31])[C:8]2=[O:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.O.O.[OH-].[Li+]>C(OCC)(=O)C>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=4)=[CH:15][C:14]=3[O:29][C:30]([F:31])([F:32])[F:33])[C:8]2=[O:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66621877HCID 66621877, compound

Product 1

HCID 66621869HCID 66621869, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine methyl 4′-((1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl)-3′-(trifluoromethoxy)biphenyl-4-carboxylate (9.15 g, 19.2 mmol), THF (175 mL) and water (175 mL) in a 500 mL flask equipped with a magnetic stir bar. While stirring in an ice bath treat the mixture with lithium hydroxide monohydrate (2.42 g, 57.7 mmol). Stir the reaction for 30 minutes, warm to room temperature and stir an additional 16 hours. Dilute with ethyl acetate (250 mL) and wash with water (250 mL). Add hydrochloric acid (2N) to the aqueous layer until it is acidic then extract with ethyl acetate (2×300 mL). Wash the extracts with aqueous saturated sodium chloride solution (1×250 mL), dry over anhydrous magnesium sulfate and concentrate to afford 6.98 g (79%) of the product as a white solid: MS (m/z): 462 (M+1).

Workup

  1. stirringStir
  2. customthe reaction for 30 minutes
  3. stirringstir an additional 16 hours
  4. washwash with water (250 mL)
  5. extractionAdd hydrochloric acid (2N) to the aqueous layer until it is acidic then extract with ethyl acetate (2×300 mL)
  6. washWash the extracts with aqueous saturated sodium chloride solution (1×250 mL)
  7. dry with materialdry over anhydrous magnesium sulfate
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-816e967d9a2c4d0fb713f444267e6e4d
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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