HCID 16110686, compound → HCID 16110712, compound

HRID 605645Notes

Reaction equation

HRID 605645 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[N:36]=[CH:35][CH:34]=[CH:33][C:28]=2[C:29]([O:31][CH3:32])=[O:30])=[CH:25][N:26]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C(C)(C)C)(C)C>CCOC(C)=O>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]([C:22]2[O:23][C:24]([C:27]3[N:36]=[CH:35][CH:34]=[CH:33][C:28]=3[C:29]([O:31][CH3:32])=[O:30])=[CH:25][N:26]=2)=[O:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 16110686HCID 16110686, compound

Product 1

HCID 16110712HCID 16110712, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from methyl 2-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)nicotinate (30 mg, 0.059 mmol) following General Procedure C. Flash chromatography (10-30% EtOAc) yielded the title compound as a white solid (17 mg, 73%): 1H NMR (CDCl3, 500 MHz) δ 8.85-8.84 (m, 1H), 8.10 (dd, 1H, J=8.0, 1.5 Hz), 7.94 (s, 1H), 7.49-7.47 (m, 1H), 7.36-7.33 (m, 2H), 7.26-7.25 (m, 3H), 4.07 (s, 3H), 3.17 (t, 2H, J=7.0 Hz), 2.69 (t, 2H, J=7.5 Hz), 1.88-1.82 (m, 2H), 1.75-1.69 (m, 2H), 1.53-1.47 (m, 4H); 13C NMR (CDCl3, 125 MHz) δ 188.5, 167.6, 152.3, 151.8, 144.3, 143.1, 137.7, 129.5, 128.8, 128.7, 127.5, 126.0, 123.9, 53.7, 39.5, 36.3, 31.7, 29.4, 29.4, 24.2; MALDI-FTMS m/z 393.1799 (M+H+, C23H25N2O4, requires 393.1809).

Sources & evidence

ORD record
ord-ba13a066aaca43bc86020f8917db2b2e
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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