Water → HCID 90203702, compound

HRID 1480223Notes

Reaction equation

HRID 1480223 reaction equation
[CH:1]1([C:4]2[C:5]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:6][C:7]([C:10]([NH:12][C:13]([C:20]3[N:24]=[C:23]([CH3:25])[O:22][N:21]=3)([CH3:19])[C:14]([O:16]CC)=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.O>C1COCC1>[CH:1]1([C:4]2[C:5]([O:26][CH2:27][C:28]([F:29])([F:30])[F:31])=[CH:6][C:7]([C:10]([NH:12][C:13]([C:20]3[N:24]=[C:23]([CH3:25])[O:22][N:21]=3)([CH3:19])[C:14]([OH:16])=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 962WaterHCID 90203258HCID 90203258, compound

Product 1

HCID 90203702HCID 90203702, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[[5-cyclopropyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonyl]amino]-2-(5-methyl-1,2,4-oxadiazol-3-yl)propanoate (example 147b, 0.295 g, 667 μmol) in a mixture of THF (4 ml)/Water (2 ml) was added LiOH monohydrate (83.9 mg, 2.00 mmol). The reaction mixture was sonicated for a few minutes to dissolved solids. The reaction was stirred at room temperature overnight. The reaction was then concentrated in vacuo and the obtained residue was dissolved in ethyl acetate. The organic phase was extracted with a 0.1M aqueous solution hydrochloric acid. The organic phase was collected and the aqueous phase was back-extracted with ethyl acetate. Combined organic phases were dried over sodium sulfate and evaporated down to dryness to yield the title compound (280 mg, 100%) as a crude yellow oil which was used without any purification. MS (ESI, m/z): 415.5 (M+H+).

Workup

  1. customThe reaction mixture was sonicated for a few minutes
  2. dissolutionto dissolved solids
  3. concentrationThe reaction was then concentrated in vacuo
  4. dissolutionthe obtained residue was dissolved in ethyl acetate
  5. extractionThe organic phase was extracted with a 0.1M aqueous solution hydrochloric acid
  6. customThe organic phase was collected
  7. extractionthe aqueous phase was back-extracted with ethyl acetate
  8. dry with materialCombined organic phases were dried over sodium sulfate
  9. customevaporated down to dryness

Sources & evidence

ORD record
ord-3667cb89dfe6416d9cb9eaf348f0b1a7
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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