Lithium Hydroxide → HCID 58934615, compound

HRID 855080Notes

Reaction equation

[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:22]([O:24]CC)=[O:23])[CH:14]([C:18]([F:21])([F:20])[F:19])[O:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:22]([OH:24])=[O:23])[CH:14]([C:18]([F:19])([F:20])[F:21])[O:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 69516476HCID 69516476, compound

Product 1

HCID 58934615HCID 58934615, compoundYield 95%

Conditions

Temperature: 40 °C

Procedure

The ester from Example 9k, Step 1 was added THF(7): EtOH(2): H2O(1) followed by LiOH (1.5 eq) and heated to 40° C. for 4 h. The reaction was cooled to room temperature, concentrated in vacuo. Acidified with HCl conc to pH 1, filtered solid and subjected solid to preparative reverse phase chromatography to produce the title compound (95%): ESHRMS m/z 333.0751 (M−H, C18H12O3F3 Calc'd 333.0733). 1HNMR (DMSO-d6/400 MHz), 13.13 (brs, 1H), 7.76 (s, 1H), 7.33 (d, 1H, J=7.5 Hz), 7.13-7.26 (m, 5H), 6.84-6.88 (m, 2H), 5.81 (q, 1H, J=7.1 Hz), 3.27 (s, 2H).

Workup

temperatureThe reaction was cooled to room temperature
concentrationconcentrated in vacuo
filtrationfiltered solid

Sources & evidence

ORD record: ord-6aabab6f7e8a45b99102bc6d3df4b693
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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