Ammonium fluoride → HCID 136343926, compound

HRID 552084Notes

Reaction equation

[CH3:1][O:2][N:3]([C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([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:4]1[NH:5][C:6](=[O:30])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:17][C@H:16]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[CH2:15][C@:14]3([C:28]#[CH:29])[F:27])[C:11]=2[N:12]=1.[F-].[NH4+]>CO>[CH3:1][O:2][N:3]([C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:4]1[NH:5][C:6](=[O:30])[C:7]2[N:8]=[CH:9][N:10]([C@@H:13]3[O:17][C@H:16]([CH2:18][OH:19])[CH2:15][C@:14]3([C:28]#[CH:29])[F:27])[C:11]=2[N:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

14 (0.35 mmol) was dissolved in MeOH (20 ml/mmol). Ammonium fluoride (3.55 mmol) was then added at room temperature and the reaction mixture was stirred at 70° C. for 2 hours. After concentration under reduced pressure, the crude material was purified by silica gel chromatography (DCM/MeOH) to yield the title compound. Beige foam. Molecular Formula C32H30FN5O4. 1H NMR (CDCl3-d6, 400 MHz) δ (ppm) 2.38-2.45 (m, 2H), 2.75 (brs, 2H), 3.64-3.67 (d, J=12.20 Hz, 2H), 3.77 (s, 4H), 4.20-4.23 (d, J=11.7 Hz, 1H), 4.41-4.42 (d, J=8.4 Hz, 1H), 5.83-5.87 (d, J=16.24 Hz, 1H), 6.80-6.82 (d, J=8.12 Hz, 4H), 7.26-7.31 (m, 11H), 7.84 (brs, 1H), 9.26 (brs, 1H)

Workup

concentrationAfter concentration under reduced pressure
customthe crude material was purified by silica gel chromatography (DCM/MeOH)

Sources & evidence

ORD record: ord-74105c0d5e724712b4091f57cba1bbcf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951789B2

Reaction notes

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