Sodium Hydroxide → HCID 18699188, compound

HRID 2290159Notes

Reaction equation

HRID 2290159 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH:26]([CH3:28])[CH3:27])[C:11]2[C:12]([CH3:25])=[C:13]([CH:22]([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+]>CO>[CH:26]([N:10]([C:11]1[C:12]([CH3:25])=[C:13]([CH:22]([CH3:24])[CH3:23])[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:29])=[O:2])=[CH:9][CH:8]=1)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54347563HCID 54347563, compound2×

Product 1

HCID 18699188HCID 18699188, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following general procedure P and using 4-[isopropyl-(7-isopropyl-3,3,6-trimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid methyl ester (Compound 67, 0.037 g, 0.096 mmol) and 1.5 mL (7.5) of 5M sodium hydroxide in 5 mL of methanol, the title compound (0.027 g, 72%) was obtained, after flash column chromatography using 15% ethyl acetate in hexanes as the eluent, as a pale yellow solid. 1H NMR (300 MHz, CDCl3): δ 7.87 (d, 2H, J=8.9 Hz), 6.59 (s, 1H), 6.42 (d, 2H, J=8.9 Hz), 4.34 (heptet, 1H, J=6.3 Hz), 4.24 (s, 2H), 3.19 (heptet, 1H, J=7.0 Hz), 1.36-1.26 (m, 15H), 0.99 (d, 3H, J=6.53 Hz).

Sources & evidence

ORD record
ord-2938d70bbfdb4514af3dc951e390c60d
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

Loading…