Methyl 6-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)picolinate → Methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)picolinate

HRID 605640Notes

Reaction equation

HRID 605640 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[N:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][CH:28]=2)=[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:32]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:30]=[CH:29][CH:28]=3)=[CH:25][N:26]=2)=[O:8])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 16110624Methyl 6-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)picolinate

Product 1

HCID 16110656Methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)picolinateYield 35.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from methyl 6-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)picolinate (70 mg, 0.138 mmol) following General Procedure C. Flash chromatography (10-30% EtOAc) yielded the title compound as a white solid (19 mg, 35%): 1H NMR (CDCl3, 500 MHz) δ 8.19 (d, 1H, J=7.0 Hz), 8.12-8.09 (m, 2H), 8.06-8.03 (m, 1H), 7.36-7.33 (m, 2H), 7.26-7.24 (m, 3H), 4.11 (s, 3H), 3.19 (t, 2H, J=7.0 Hz), 2.69 (t, 2H, J=7.5 Hz), 1.89-1.83 (m, 2H), 1.75-1.69 (m, 2H), 1.55-1.47 (m, 4H); 13C NMR (CDCl3, 125 MHz) δ 188.9, 165.5, 158.0, 152.7, 149.0, 147.0, 143.1, 138.7, 128.8, 128.7, 128.4, 126.0, 125.6, 123.7, 53.5, 39.6, 36.3, 31.7, 29.4, 29.4, 24.3; MALDI-FTMS m/z 393.1796 (M+H+, C23H25N2O4, requires 393.1809).

Sources & evidence

ORD record
ord-cdd0b5ba36f24890b87e9ae54abdfaae
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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