Ethyl Acetate → HCID 9800843, compound

HRID 2290161Notes

Reaction equation

C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:27]([CH3:29])[CH3:28])[C:11]2[C:12]([CH3:26])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:14]3[O:18][CH2:17][C:16]([CH3:20])([CH3:19])[C:15]=3[CH:21]=2)=[CH:6][CH:5]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[CH:27]([N:10]([C:11]1[C:12]([CH3:26])=[C:13]([C:22]([CH3:23])([CH3:25])[CH3:24])[C:14]2[O:18][CH2:17][C:16]([CH3:19])([CH3:20])[C:15]=2[CH:21]=1)[C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:30])=[O:2])=[CH:9][CH:8]=1)([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-[isopropyl-(7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid methyl ester (Compound 69, 0.015 g, 0.038 mmol) in 3 mL of ethanol was treated with 1M sodium hydroxide (1.5 mL, 1.5 mmol) and the resulting clear solution was heated at 80° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was neutralized with saturated ammonium chloride solution and extracted with diethylether. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to afford, after flash column chromatography using 25% ethyl acetate in hexanes as the eluent, the title compound (0.007 g, 48%) as a solid. 1H NMR (300 MHz, CDCl3): δ 7.87 (d, 2H, J=9.1 Hz), 6.61 (s, 1H), 6.43 (d, 2H, J=8.9 Hz), 4.32 (heptet, 1H, J=6.5 Hz), 4.18 (s, 2H), 3.83 (s, 1H), 2.19 (s, 3H), 1.52 (s, 9H), 1.32-1.28 (m, 9H), 0.99 (d, 3H, J=6.6 Hz).

Workup

customThe volatiles were removed by distillation in vacuo
extractionextracted with diethylether
extractionThe organic extract
dry with materialwas dried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
customto afford

Sources & evidence

ORD record: ord-557a2c68121c40abbe909a198c8fb480
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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