Lithium Hydroxide → HCID 73507791, compound

HRID 1774559Notes

Reaction equation

[C:1]([O:5][CH:6]([C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]=1[C:23]1[CH:24]=[CH:25][C:26]2[O:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:32]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.CO.[OH-].[Li+]>O>[C:1]([O:5][CH:6]([C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]=1[C:23]1[CH:24]=[CH:25][C:26]2[O:31][CH2:30][CH2:29][CH2:28][C:27]=2[CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of methyl 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-phenyl-1H-pyrazol-5-yl]acetate (2c) (48 mg, 0.11 mmol) in a 1/1 mixture of tetrahydrofurane/methanol (2 mL) was added a solution of lithium hydroxide (11 mg, 0.44 mmol) in water (0.25 mL). The mixture was stirred at 65° C. for 2 hours. TLC analysis showed no more starting material. The mixture was concentrated under reduced pressure. Water (0.5 mL) and ethyl acetate (2 mL) were added to the residue. The aqueous layer was acidified with 1M hydrochloric acid until pH 5 and extracted with ethyl acetate (3×2 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to provide 2-(tert-butoxy)-2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-3-phenyl-1H-pyrazol-5-yl]acetic acid (example 2) (40 mg, 0.095 mmol, 85%) as a white solid.

Workup

concentrationThe mixture was concentrated under reduced pressure
additionWater (0.5 mL) and ethyl acetate (2 mL) were added to the residue
extractionextracted with ethyl acetate (3×2 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2f3fc9b1b2204edd8ae28e191fe75215
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260395B2

Reaction notes

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