Water → HCID 90214926, compound

HRID 1480255Notes

Reaction equation

HRID 1480255 reaction equation
[F:1][C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:33])([F:32])[F:31])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[C:16]([O:18]CC)=[O:17])=[O:13])=[N:10][CH:11]=2)[CH2:5][O:4][CH2:3]1.O>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1([C:6]2[C:7]([O:28][C@@H:29]([CH3:34])[C:30]([F:31])([F:33])[F:32])=[CH:8][C:9]([C:12]([NH:14][C:15]([C:22]3[N:26]=[C:25]([CH3:27])[O:24][N:23]=3)([CH3:21])[C:16]([OH:18])=[O:17])=[O:13])=[N:10][CH:11]=2)[CH2:5][O:4][CH2:3]1

Participants

5

Reactant 2

HCID 962WaterHCID 90214978HCID 90214978, compound

Product 1

HCID 90214926HCID 90214926, compoundYield 127.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-[[5-(3-fluorooxetan-3-yl)-4-[(1S)-2,2,2-trifluoro-1-methyl-ethoxy]pyridine-2-carbonyl]amino]-2-(5-methyl-1,2,4-oxadiazol-3-yl)propanoate (example 183a, 150 mg, 306 μmol) in a mixture of THF (2 ml)/water (1 ml) was added LiOH monohydrate (25.7 mg, 612 μmol). The reaction mixture was sonicated to dissolve the solids. The reaction was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and extracted with 1 mL of an aqueous solution 2M trifluoroacetic 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. The crude material was dissolved in toluene and evaporated down to dryness to yield to yield the title compound (180 mg, 100%) as a crude solid which was used without any purification. MS (ESI, m/z): 463.5 (M+H+).

Workup

  1. customThe reaction mixture was sonicated
  2. dissolutionto dissolve the solids
  3. extractionextracted with 1 mL of an aqueous solution 2M trifluoroacetic acid
  4. customThe organic phase was collected
  5. extractionthe aqueous phase was back-extracted with ethyl acetate
  6. dry with materialCombined organic phases were dried over sodium sulfate
  7. customevaporated down to dryness
  8. dissolutionThe crude material was dissolved in toluene
  9. customevaporated down to dryness
  10. customto yield

Sources & evidence

ORD record
ord-acee44f866b546fba514805d53d9bb38
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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