HCID 16110608, compound → HCID 16110640, compound

HRID 605636Notes

Reaction equation

HRID 605636 reaction equation
[Si]([O:8][CH:9]([C:22]1[O:23][C:24]([C:27]2[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=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>[OH:33][C:29]1[CH:28]=[C:27]([C:24]2[O:23][C:22]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:26][CH:25]=2)[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 1

HCID 16110608HCID 16110608, compound

Product 1

HCID 16110640HCID 16110640, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 3-(2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)oxazol-5-yl)phenol (29 mg, 0.062 mmol) following General Procedure D. Preparative thin layer chromatography (30% EtOAc) yielded the title compound as a white solid (5.2 mg, 27%): 1H NMR (CD3OD, 500 MHz) δ 7.74 (s, 1H), 7.38-7.37 (m, 2H), 7.32-7.29 (m, 3H), 7.24-7.23 (m, 2H), 7.21-7.20 (m, 1H), 6.95-6.94 (m, 1H), 3.14 (t, 2H, J=7.0 Hz), 2.69 (t, 2H, J=7.5 Hz), 1.85-1.79 (m, 2H), 1.75-1.69 (m, 2H), 1.54-1.42 (m, 4H); 13C NMR (CD3OD, 125 MHz) δ 188.5, 158.4, 157.4, 154.7, 142.9, 130.5, 128.4, 128.2, 128.2, 125.6, 123.9, 117.2, 116.5, 111.7, 38.7, 35.8, 31.5, 29.0, 29.0, 23.9; MALDI-FTMS m/z 350.1752 (M+H+, C22H24NO3, requires 350.1751).

Sources & evidence

ORD record
ord-98d1bc089c184e4fa290f8933007cd8a
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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