Hydrochloric Acid → HCID 67125571, compound

HRID 1184920Notes

Reaction equation

[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:21])=[C:16]([CH:20]=1)[C:17]([O-:19])=[O:18])=[O:10])([CH3:5])[CH3:4])#[N:2].[OH-].[Li+].Cl>C1COCC1.O>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:22]=[CH:23][CH:24]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:21])=[C:16]([CH:20]=1)[C:17]([OH:19])=[O:18])=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylbenzoate 103 (7.13 mmol, 2.5 g) in THF (30 mL), lithium hydroxide (28.5 mmol, 0.683 g) in (20 mL) water was added and the reaction was stirred overnight at 40° C. The reaction mixture was acidified with 2N HCl solution and extracted with ethyl acetate (2×). Organic layer was washed with 2N NaOH (3×), aqueous layer was acidified with 2N HCl solution and the milky mixture was extracted with ethyl acetate (3×), dried and concentrated under reduced pressure. Crude product was triturated with ACN to give 5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylbenzoic acid 104 (550 mg, 23%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.50 (s, 3H), 7.30 (d, J=8.6 Hz, 1H), 7.60 (t, J=7.4 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.90 (dd, J=8.2 Hz and 2.3 Hz, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.06 (t, J=2.0 Hz, 1H), 8.24 (d, J=2.3 Hz, 1H), 10.40 (s, 1H). (m/z)=323 (M+H)+.

Workup

extractionextracted with ethyl acetate (2×)
washOrganic layer was washed with 2N NaOH (3×), aqueous layer
extractionthe milky mixture was extracted with ethyl acetate (3×)
customdried
concentrationconcentrated under reduced pressure
customCrude product was triturated with ACN

Sources & evidence

ORD record: ord-6979ef0e388649b6b03396f5b7b8c09b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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