Sodium Hydroxide → HCID 44580027, compound

HRID 1992933Notes

Reaction equation

HRID 1992933 reaction equation
[CH2:1]([C:5]1[C:6]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([O:26]CC)=[O:25])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CCO>[CH2:1]([C:5]1[C:6]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86616663HCID 86616663, compound

Product 1

HCID 44580027HCID 44580027, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (162) (0.25 g, 0.52 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.21 g (88%) of compound 163 as a white solid. mp 186-187° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.78 (t, J=7.3 Hz, 3H), 1.15-1.29 (m, 2H), 1.40-1.50 (m, 2H), 2.62 (t, J=7.3 Hz, 2H), 3.75 (s, 3H), 6.26 (d, J=15.9 Hz, 1H), 6.56 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.6 Hz, 2H), 7.07 (d, J=8.6 Hz, 2H), 7.30-7.40 (m, 3H), 7.47 (t, J=7.5 Hz, 1H), 7.53 (d, J=16.0 Hz, 1H), 7.50-7.56 (m, 2H), 7.89 (d, J=8.2 Hz, 1H). LCMS (ESI): m/z 453 (M+H)+, m/z 451 (M−H)−.

Sources & evidence

ORD record
ord-1abded4ffdb743598185c6d9933b24c9
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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