Sodium Hydroxide → HCID 18699174, compound

HRID 2290160Notes

Reaction equation

HRID 2290160 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:27][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+]>CO>[CH2:27]([N:10]([C:11]1[C:12]([CH3:26])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:14]2[O:18][CH2:17][C:16]([CH3:20])([CH3:19])[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]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54082430HCID 54082430, compound2×

Product 1

HCID 18699174HCID 18699174, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following general procedure P and using 4-[ethyl-(7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid methyl ester (Compound 68, 0.11 g, 0.29 mmol) and 2 mL (7.5) of 5M sodium hydroxide in 5 mL of methanol, the title compound (0.025 g, 23%) was obtained as a pale yellow solid, after flash column chromatography using 25% ethyl acetate in hexanes as the eluent followed by recrystallization from hexanes. 1H NMR (300 MHz, CDCl3): δ 7.88 (d, 2H, J=9.0 Hz), 6.70 (s, 1H), 6.43 (d, 2H, J=9.0 Hz), 4.17 (s, 2H), 3.88-3.76 (m, 1H), 3.45-3.30 (m, 1H), 2.20 (s, 3H), 1.52 (s, 9H), 1.28-1.24 (m, 9H).

Sources & evidence

ORD record
ord-52e764c2183a4fabbf8598e952aacf90
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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