Tetrabutylammonium Fluoride → HCID 57385087, compound

HRID 1427783Notes

Reaction equation

HRID 1427783 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:49]=[CH:50][CH:51]=1)[CH2:10][C@H:11]1[C:36](=[O:37])[N:35]2[NH:38][C@@H:31]([CH2:32][CH2:33][CH2:34]2)[C:30](=[O:39])[O:29][CH2:28][C:27]2=[CH:40][C:23](=[CH:24][CH:25]=[N:26]2)[CH:22]=[CH:21][CH2:20][CH2:19][C@@H:18]([O:41][CH3:42])[C@@H:17]([CH3:43])[C:16](=[O:44])[NH:15][C@@H:14]([CH:45]([CH3:47])[CH3:46])[C:13](=[O:48])[NH:12]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[OH:6][C:7]1[CH:8]=[C:9]([CH:49]=[CH:50][CH:51]=1)[CH2:10][C@H:11]1[C:36](=[O:37])[N:35]2[NH:38][C@@H:31]([CH2:32][CH2:33][CH2:34]2)[C:30](=[O:39])[O:29][CH2:28][C:27]2[CH:40]=[C:23]([CH:24]=[CH:25][N:26]=2)[CH:22]=[CH:21][CH2:20][CH2:19][C@@H:18]([O:41][CH3:42])[C@@H:17]([CH3:43])[C:16](=[O:44])[NH:15][C@@H:14]([CH:45]([CH3:47])[CH3:46])[C:13](=[O:48])[NH:12]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71225675HCID 71225675, compound

Product 1

HCID 57385087HCID 57385087, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (E)-(1S,14R,15R,18S,21S)-21-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-18-isopropyl-14-methoxy-15-methyl-3-oxa-6,17,20,23,27-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-5(28),6,8,10-tetraene-2,16,19,22-tetraone (160 mg, 0.21 mmol) in tetrahydrofuran (10 mL) was stirred at 0° C. under nitrogen. A solution of tetra-N-butylammonium fluoride (1 M in tetrahydrofuran, 0.34 mL, 0.34 mmol) was added and the reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for 15 minutes. Silica gel was added and the solvent was evaporated. The residue was purified by silica gel chromatography using a gradient of ethyl acetate to ethyl acetate/acetone 9:1 to afford the title compound (88 mg, 65%) as a white solid. 1H NMR (300 MHz, CD3CN) δ 0.97 (d, J=7.1 Hz, 3H), 0.99 (d, J=7.1 Hz, 3H), 1.32 (d, J=7.4 Hz, 3H), 1.60-2.20 (m, 9H), 2.55-2.89 (m, 4H), 3.28-3.34 (m, 1H), 3.46 (s, 3H), 3.62-3.69 (m, 1H), 4.19-4.41 (m, 3H), 5.19 (d, J=14.5 Hz, 1H), 5.35 (d, J=14.5 Hz, 1H), 5.58-5.65 (m, 1H), 5.83 (d, J=15.8 Hz, 1H), 6.30-6.39 (m, 1H), 6.51 (dd, J=7.9, 1.6 Hz, 1H), 6.67 (d, J=7.6 Hz, 1H), 6.75-6.81 (m, 1H), 7.01-7.07 (m, 3H), 7.22-7.28 (m, 2H), 8.02 (s, 1H), 8.39 (d, J=5.1 Hz, 1H).

Workup

  1. waitat room temperature for 15 minutes
  2. additionSilica gel was added
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d3e4da2212104543a4132a7bafb1427b
Source dataset
uspto-grants-2015_01
Patent number
US08933015B2

Reaction notes

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