Sodium Hydroxide → HCID 9841482, compound

HRID 2290170Notes

Reaction equation

C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH:25]([CH3:27])[CH3:26])[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>[CH: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([CH3:24])[CH3:23])[C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:28])=[O:3])=[CH:10][CH:9]=1)([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 4-[i-propyl-(1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 86, 0.007 g) in 5 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 preparative reverse phase HPLC, using 10% water in acetonitrile as the mobile phase, to afford the title compound (0.0064, 90%) as a white solid. 1H NMR (300 MHz, acetone-d6): δ 7.78 (d, 2H, J=8.9 Hz), 7.32 (d, 1H, J=7.8 Hz), 7.04 (dd, 1H, J=7.8 J=1.8 Hz), 7.00 (d, 1H, J=1.7 Hz), 6.56 (d, 2H, J=9.0 Hz), 4.46 (heptet, 1H, J=6.5 Hz), 1.50 (s, 6H), 1.47 (s, 6H), 1.15 (d, 6H, J=6.5 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-89f3da5fae9f4098b3ad284333ddac0a
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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