Sodium Hydroxide → HCID 9864033, compound

HRID 2290168Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 4-[n-butyl-(1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 82, 0.224 g, 0.6 mmol) in 20 mL of ethanol was treated with 2 mL of 5M sodium hydroxide solution and the resulting solution was heated at 55° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was acidified using hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate and evaporated to a residue which was subjected to flash column chromatography on silica gel using ethyl acetate as the eluent to afford the title compound (0.091 g, 50%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.90 (d, 2H, J=9.1 Hz), 7.12 (d, 1H, J=8.2 Hz), 7.09 (d, 1H, J=8.1 Hz), 6.91 (s, 1H), 6.67 (d, 2H, J=9.0 Hz), 3.71 (t, 2H, J=7.8 Hz), 1.72-1.64 (m, 2H) 1.56 (s, 6H), 1.52 (s, 6H), 1.34-1.45 (m, 2H), 0.95 (t, 3H, J=7.3 Hz).

Workup

customThe volatiles were removed by distillation in vacuo
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated to a residue which

Sources & evidence

ORD record: ord-ddae0961283c4ac7be0bd7ae7ecd8d0a
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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