Trifluoroacetic acid → HCID 67015698, compound

HRID 1618033Notes

Reaction equation

HRID 1618033 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1[CH:14]=[C:13]([C:15](=[O:42])[CH2:16][C@H:17]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]3[CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32]3)=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:24])[CH:12]=[CH:11][N:10]=1>ClCCl>[NH:33]1[CH2:34][CH:31]([C:28]2[CH:29]=[CH:30][C:25]([C@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[CH2:16][C:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([CH3:8])[CH:14]=3)=[O:42])=[CH:26][CH:27]=2)[CH2:32]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67015759HCID 67015759, compound

Product 1

HCID 67015698HCID 67015698, compoundYield 115.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.37 g, 927 μl, 12.0 mmol) was added at 0° C. to a solution of (R)-tert-butyl 3-(4-(3-(2-methylpyridin-4-yl)-3-oxo-1-o-tolylpropyl)phenyl)azetidine-1-carboxylate (283 mg, 601 μmol, Eq: 1.00) in dichloromethane (2 mL). The ice bath was removed, then after 2 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated to afford the title compound (258 mg, purity ca. 85%), which was used for the next step without purification. Off-white foam, MS (ESI+): m/z=371.0 ([M+H]+).

Workup

  1. customThe ice bath was removed
  2. customafter 2 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e663ecd17d35428f81c04f097541a804
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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