Lithium Hydroxide → HCID 58934991, compound

HRID 855081Notes

Reaction equation

[CH3:1][C:2]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([O:21]CC)=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][CH:6]=1.[Li+].[OH-]>>[CH3:1][C:2]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:3]=1[CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([C:19]([OH:21])=[O:20])[CH:11]([C:15]([F:18])([F:17])[F:16])[O:12]2)=[CH:7][CH:6]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 69518815HCID 69518815, compound

Product 1

HCID 58934991HCID 58934991, compoundYield 93%

Conditions

Temperature: 40 °C

Procedure

The ester from Example 9s, Step 5 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 (93%): ESHRMS m/z 361.1062 (M−H, C20H16O3F3Calc'd 361.1046). 1HNMR (DMSO-d6/400 MHz), 13.19 (s, 1H), 7.77 (s, 1H), 7.33 (d, 1H, J=7.6 Hz), 7.00 (m, 3H), 6.77 (d, 1H, J=7.7 Hz), 6.70 (s, 1H), 5.82 (q, 1H, J=7.1 Hz), 3.87 (s, 2H), 2.2 (s, 3H), 2.10 (s, 3H).

Workup

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

Sources & evidence

ORD record: ord-0532f2d48a0b407b9031ed7ee5d09230
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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