Sodium Hydroxide → HCID 44580026, compound

HRID 1992938Notes

Reaction equation

HRID 1992938 reaction equation
[CH2:1]([C:5]1[C:6]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[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]([F:35])=[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 86616664HCID 86616664, compound

Product 1

HCID 44580026HCID 44580026, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl ester (168) (0.25 g, 0.53 mmol) was saponified with 1 N NaOH in THF and EtOH to give 0.18 g (79%) of the title compound (169) as a white solid. mp 169-170° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.78 (t, J=7.3 Hz, 3H), 1.15-1.28 (m, 2H), 1.40-1.50 (m, 2H), 2.60 (t, J=7.9 Hz, 2H), 6.27 (d, J=16.0 Hz, 1H), 6.56 (d, J=8.6 Hz, 2H), 7.01 (t, J=8.7 Hz, 2H), 7.12-7.22 (m, 2H), 7.32-7.42 (m, 3H), 7.46-7.56 (m, 2H), 7.70-7.80 (m, 2H), 7.90 (d, J=8.2 Hz, 1H). LCMS (ESI): m/z 441 (M+H)+, m/z 439 (M−H)−. Anal. Calc for C29H25FO3.0.1H2O: C, 78.75; H, 5.74. Found: C, 78.85; H, 5.64.

Sources & evidence

ORD record
ord-f72e006260da40e89910637a9d89853c
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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