Tetrabutylammonium Fluoride → HCID 86702893, compound

HRID 1849550Notes

Reaction equation

HRID 1849550 reaction equation
[C:1]12([CH2:11][O:12][C:13]3[C:46]([CH:47]4[CH2:49][CH2:48]4)=[CH:45][C:16]([C:17]([NH:19][S:20]([N:23]4[CH2:26][CH:25]([O:27][Si](C(C)(C)C)(C5C=CC=CC=5)C5C=CC=CC=5)[CH2:24]4)(=[O:22])=[O:21])=[O:18])=[C:15]([F:50])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[C:1]12([CH2:11][O:12][C:13]3[C:46]([CH:47]4[CH2:48][CH2:49]4)=[CH:45][C:16]([C:17]([NH:19][S:20]([N:23]4[CH2:26][CH:25]([OH:27])[CH2:24]4)(=[O:22])=[O:21])=[O:18])=[C:15]([F:50])[CH:14]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86702894HCID 86702894, compound

Product 1

HCID 86702893HCID 86702893, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(adamantan-1-ylmethoxy)-N-((3-((tert-butyldiphenylsilyl)-oxy)azetidin-1-yl)sulfonyl)-5-cyclopropyl-2-fluorobenzamide (0.28 g, 0.39 mmol) in anhydrous dichloromethane (10 mL) was added tetrabutylammonium fluoride solution (1.0 M in tetrahydrofuran, 1.6 mL, 1.56 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 2 h. The mixture was quenched with aqueous hydrochloride acid solution (1N, 30 mL) followed by extraction with ethyl acetate (100 mL). The organic layer was washed with water (30 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo, the residue was purified by silica gel column chromatography using 10%-100% gradient ethyl acetate (containing 0.2% acetic acid) in hexanes to afford the title compound as an off-white solid (0.07 g, 36%): 1H NMR (300 MHz, DMSO-d6) δ 11.62 (s, 1H), 7.15 (d, J=8.3 Hz, 1H), 6.93 (d, J=13.0 Hz, 1H), 5.83 (d, J=6.0 Hz, 1H), 4.45-4.35 (m, 1H), 4.14-4.09 (m, 2H), 3.89-3.84 (m, 2H), 3.65 (s, 2H), 2.09-1.99 (m, 4H), 1.75-1.67 (m, 12H), 0.94-0.88 (m, 2H), 0.69-0.66 (m, 2H); MS (ES+) m/z 479.3 (M+1); MS (ES−) m/z 477.4 (M−1).

Workup

  1. customThe mixture was quenched with aqueous hydrochloride acid solution (1N, 30 mL)
  2. extractionfollowed by extraction with ethyl acetate (100 mL)
  3. washThe organic layer was washed with water (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c96a8bcf496243578ecc45bfd6e56bfb
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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