Tetrabutylammonium Fluoride → HCID 86605354, compound

HRID 132523Notes

Reaction equation

HRID 132523 reaction equation
[Si]([O:8][CH2:9][CH:10]([O:44][C:45]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([O:52][CH3:53])[CH:47]=1)[CH2:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([C:25]([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)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[N:17][C:18]=2[NH:22][O:23][CH3:24])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH:10]([O:44][C:45]([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[C:48]([O:52][CH3:53])[CH:47]=1)[CH2:11][CH2:12][N:13]1[CH:21]=[N:20][C:19]2[C:14]1=[N:15][C:16]([C:25]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[N:17][C:18]=2[NH:22][O:23][CH3:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131726925HCID 131726925, compound

Product 1

HCID 86605354HCID 86605354, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15 (10.6 g, 12.02 mmol) in THF (120 mL) is treated with tetrabutyl ammonium fluoride (1M in THF, 12.1 mL) and the reaction mixture stirred at room temperature for 2 h followed by concentration. The residue is purified on a silica gel column using ethyl acetate:hexanes:methanol (1:1:0 to 1:1:0.1) to give 8.87 g (96%) of 16 as a white solid: 1H NMR (DMSO-d6): δ 8.21 (s, 1H), 7.92 (s, 1H), 7.38-7.05 (m, 25H), 6.89 (d, J=9.1 Hz, 2H), 6.82 (d, J=9.0 Hz, 2H), 5.09 (t, J=5.4 Hz, 1H), 4.88-4.77 (m, 1H), 3.77-3.70 (m, 2H), 3.76 (s, 3H), 3.73 (s, 3H), 2.96-2.76 (m, 2H), 2.44-2.27 (m, 1H), 2.27-2.11 (m, 1H). IR (KBr, cm−1) 3412, 2932, 1734, 1606, 1509, 1251 and 1033. Anal. Calcd for C49H45N5O4.0.25 H2O.0.4 EtOAc: C, 75.25; H, 6.08; N, 8.67. Found: C, 75.35; H, 6.04; N, 8.50.

Workup

  1. concentrationfollowed by concentration
  2. customThe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-6942ab800c5c4ec48574efd2cd66c399
Source dataset
uspto-grants-2008_06
Patent number
US07388002B2

Reaction notes

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