Sodium Hydroxide → HCID 11604240, compound

HRID 1992954Notes

Reaction equation

HRID 1992954 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[O:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CCO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([C:18]([F:20])([F:21])[F:19])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[O:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68536273HCID 68536273, compound

Product 1

HCID 11604240HCID 11604240, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl ester (189) (63 mg, 0.15 mmol) was saponified with 1 N NaOH in THF and EtOH to give 48 mg (79%) of the title compound (190) as a white solid. mp 244-245° C. 1H NMR (400 MHz, CH3OH-d4): δ 6.60 (d, J=8.8 Hz, 2H), 6.64 (d, J=8.6 Hz, 2H), 6.96 (d, J=8.4 Hz, 2H), 7.60-7.72 (m, 2H), 7.79 (d, J=9.0 Hz, 2H), 7.88 (d, J=8.1 Hz, 1H), 8.15 (d, J=7.9 Hz, 1H), 8.34 (s, 1H). LCMS (ESI): m/z 447 (M+Na)+, m/z 423 (M−H)−. Anal. Calc for C24H15F3O4.0.25H2O: C, 67.21; H, 3.64. Found: C, 67.05; H, 3.47.

Sources & evidence

ORD record
ord-bd31afba9f264355a3ba26093b55c884
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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