Tetrabutylammonium Fluoride → (2S)-3-hydroxy-2-(2-(1-(2,2,2-trifluoro ethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yloxy)propanamide

HRID 886507Notes

Reaction equation

HRID 886507 reaction equation
C([Si](C)(C)[O:6][CH2:7][C@H:8]([O:12][C:13]1[CH:36]=[CH:35][C:16]2[C:17]3[N:21]([CH2:22][CH2:23][O:24][C:15]=2[CH:14]=1)[CH:20]=[C:19]([C:25]1[N:26]([CH2:30][C:31]([F:34])([F:33])[F:32])[N:27]=[CH:28][N:29]=1)[N:18]=3)[C:9]([NH2:11])=[O:10])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C.O>[OH:6][CH2:7][C@H:8]([O:12][C:13]1[CH:36]=[CH:35][C:16]2[C:17]3[N:21]([CH:20]=[C:19]([C:25]4[N:26]([CH2:30][C:31]([F:32])([F:33])[F:34])[N:27]=[CH:28][N:29]=4)[N:18]=3)[CH2:22][CH2:23][O:24][C:15]=2[CH:14]=1)[C:9]([NH2:11])=[O:10]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58204709HCID 58204709, compound

Product 1

HCID 58204856(2S)-3-hydroxy-2-(2-(1-(2,2,2-trifluoro ethyl)-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yloxy)propanamideYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-(tert-butyl-dimethyl-silanyloxy)-2-{2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yloxy}-propionamide (101 mg, 0.18 mmol) in THF (5 mL) was added TBAF (0.22 mL, 1M solution in THF, 0.22 mmol) and the reaction mixture was stirred at RT for 2 hr. The reaction mixture was diluted with ethyl acetate (10 mL) and water (10 mL) added. A white precipitate formed which was collected by filtration and dried in vacuo to yield 513 as a white solid (45 mg, 56%). LCMS: RT=2.98 min, [M+H]+=439; 1H NMR (400 MHz, d6-DMSO) 8.23 (1H, d, J=8.7 Hz), 8.03 (1H, s), 7.96 (1H, s), 7.50 (1H, br s), 7.30 (1H, br s), 6.77 (1H, dd, J=8.9, 2.7 Hz), 6.54 (1H, d, J=2.6 Hz), 5.86 (2H, q, J=8.9 Hz), 5.09 (1H, t, J=5.8 Hz), 4.54 (1H, t, J=4.9 Hz), 4.50-4.41 (4H, m), 3.74-3.67 (2H, m)

Workup

  1. additionadded
  2. customA white precipitate formed which
  3. filtrationwas collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9142a41e01f94bee8f2901932117b077
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

Loading…