Tetrabutylammonium Fluoride → HCID 22235789, compound

HRID 1744085Notes

Reaction equation

HRID 1744085 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][N:29](C(O[Si](C(C)C)(C(C)C)C(C)C)=O)[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([CH2:3][NH:4][C:5]([C:7]1([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[CH:22][CH:21]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22236163HCID 22236163, compound

Product 1

HCID 22235789HCID 22235789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of triisopropylsilyl 4-{2′-[(1-{[(cyanomethyl)amino]carbonyl}-cyclohexyl)sulfanyl][1,1′-biphenyl]-4yl}-1-piperazinecarboxylate (35 mg, 0.055 mmol) in THF (8 mL) was added TBAF (1 M in THF, 0.08 mL). The solution was stirred at 0° C. for 20 min, then partitioned between EtOAc and saturated aq. NaHCO3. The organic phase was washed with water and brine, then dried over MgSO4 and concentrated and placed under vacuum for 6 h to give N-(cyanomethyl)-1-{[4′-(1-piperazinyl)[1,1 ′-biphenyl]-2-yl]sulfanyl}cyclohexanecarboxamide. MS (+APCI) m/z 435 (M+1, 40), 351 (100), 318 (45).

Workup

  1. custompartitioned between EtOAc and saturated aq. NaHCO3
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. waitplaced under vacuum for 6 h

Sources & evidence

ORD record
ord-ca39127a99cc433493e1fa577ef02fbc
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

Loading…