Triethylamine → HCID 86661737, compound

HRID 1961541Notes

Reaction equation

HRID 1961541 reaction equation
F.F.F.C(N(CC)CC)C.C(N(CC)CC)C.[B-](F)(F)(F)F.CCN([S+](F)[F:29])CC.[CH:31]([N:44]1[CH2:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([C:55]3[CH2:59][C:58]([C:64]4[CH:69]=[C:68]([Cl:70])[C:67]([Cl:71])=[C:66]([Cl:72])[CH:65]=4)([C:60]([F:63])([F:62])[F:61])[O:57][N:56]=3)=[CH:51][C:50]=2[Br:73])(O)[CH2:45]1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl>[CH:31]([N:44]1[CH2:45][C:46]([C:49]2[CH:54]=[CH:53][C:52]([C:55]3[CH2:59][C:58]([C:64]4[CH:69]=[C:68]([Cl:70])[C:67]([Cl:71])=[C:66]([Cl:72])[CH:65]=4)([C:60]([F:63])([F:62])[F:61])[O:57][N:56]=3)=[CH:51][C:50]=2[Br:73])([F:29])[CH2:47]1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 44517918(Diethylamino)(difluoro)sulfanium tetrafluoroborateHCID 71623197HCID 71623197, compound

Product 1

HCID 86661737HCID 86661737, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Triethylamine trihydrofluoride (0.3 mL, 1.7 mmol) and triethylamine (0.11 mL, 0.8 mL) were dissolved in dichloromethane (30 mL) and cooled to −78° C. To the cooled mixture was added XtalFluor-E (310 mg, 1.4 mmol) and then 1-benzhydryl-3-(2-bromo-4-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)azetidin-3-ol (Preparation 28, 600 mg, 0.8 mmol). Cooling was removed and the mixture was allowed to warm to room temperature with stirring for 2 hours. The reaction was poured into saturated aqueous sodium carbonate solution (100 mL) and the organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. Crude material was chromatographed (40 G Redi-Sep Column) eluting from 100% heptane to 20:80 EtOAc:heptane to afford the intermediate (523 mg, 87%) as a glass. 1HNMR (CDCl3) δ ppm: 7.90 (1H), 7.69-7.66 (3H), 7.47-7.21 (11H), 4.46 (1H), 4.08 (1H), 3.90-3.66 (5H); m/z (Cl) 713 ([M+H]+.

Workup

  1. temperatureCooling
  2. customwas removed
  3. temperatureto warm to room temperature
  4. additionThe reaction was poured into saturated aqueous sodium carbonate solution (100 mL)
  5. customthe organic phase was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customCrude material was chromatographed (40 G Redi-Sep Column)
  10. washeluting from 100% heptane to 20:80 EtOAc

Sources & evidence

ORD record
ord-354a46f8839944829de512fc35f44f6c
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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