Potassium Hydroxide → HCID 69053921, compound

HRID 2103069Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2([C:15]([O:17]CC)=[O:16])[CH2:14][CH2:13][CH2:12]2)=[C:5]([CH3:20])[C:4]=1[CH3:21].[OH-].[K+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13][CH2:12]2)=[C:5]([CH3:20])[C:4]=1[CH3:21]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of ethyl 1-((4-methoxy-2,3-dimethylphenylamino)methyl)-cyclobutanecarboxylate (19 g) in ethanol (120 mL) was added KOH (9 g in 50 mL of water). The solution was then heated up in an 85° C. bath for 2 hours. The solution was then evaporated to dryness, HCl (3 M) was then added while the flask cooled in ice bath to reach a pH of less than 1, and the solution was extracted with ethylacetate. The combined organic phases were then dried and evaporated to give 1-((4-methoxy-2,3-dimethylphenylamino)methyl)cyclobutanecarboxylic acid (21.0 g), which was used in the next step without further purification. 1H-NMR (300 MHz, CDCl3) δ=8.78-7.95 (s, 1H), 6.81-6.74 (d, 1H), 6.73-6.66 (d, 1H), 3.77 (s, 3H), 3.44 (s, 2H), 2.68-2.41 (m, 2H), 2.17 (s, 3H); 2.14 (s, 3H), 2.09-1.93 (m, 4H) ppm. 13C-NMR (75 MHz, CDCl3) δ=181.21, 15.251, 137.65, 126.32, 125.78, 112.31, 108.99, 56.21, 52.84, 46.64, 28.46, 15.93, 13.36, 12.27 ppm.

Workup

customThe solution was then evaporated to dryness, HCl (3 M)
additionwas then added while the flask
temperaturecooled in ice bath
extractionthe solution was extracted with ethylacetate
customThe combined organic phases were then dried
customevaporated

Sources & evidence

ORD record: ord-de27b612ae284cf3997b7f68f95557e5
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576094B2

Reaction notes

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