Water → HCID 178493765, compound

HRID 869637Notes

Reaction equation

HRID 869637 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([C@H:21]2[CH2:26][CH2:25][C@H:24]([C:27]([F:30])([F:29])[F:28])[CH2:23][CH2:22]2)=[O:20])[C:6]([C:9]([O-:11])=[O:10])=[N:7][CH:8]=1.[OH-].[Na+].O.C(OCC)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:12][CH2:13][C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([C@H:21]2[CH2:26][CH2:25][C@H:24]([C:27]([F:30])([F:28])[F:29])[CH2:23][CH2:22]2)=[O:20])[C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 178493764HCID 178493764, compound

Product 1

HCID 178493765HCID 178493765, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-methoxy-3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinate (170 mg, 0.37 mmol, EXAMPLE 31 Step 3) in tetrahydrofuran was added 2 N aq. sodium hydroxide (0.5 mL, 1.00 mmol) at room temperature. After being stirred at room temperature for 24 h, water and diethylether were added to the mixture. The aqueous layer was washed with diethylether and acidified with 2 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated in vacuo to afford 151 mg (95%) of the title compound as an oil. The residual oil was used for the next step without further purification.

Workup

  1. washThe aqueous layer was washed with diethylether
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55dc77bc4ed3467dbf525fa0b99a3ddd
Source dataset
uspto-grants-2015_03
Patent number
US08969383B2

Reaction notes

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