HCID 59132670, compound → HCID 59132797, compound

HRID 1993054Notes

Reaction equation

HRID 1993054 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH:19](C(O)=O)[C:20]([OH:22])=[O:21])[CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH:15]=[C:16]([CH3:17])[CH3:18])[CH2:19][C:20]([OH:22])=[O:21])=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 59132670HCID 59132670, compound

Product 1

HCID 59132797HCID 59132797, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of compound 33.3 (0.136 mmol) in toluene was refluxed for 16 h. After removing the solvent, the residue was purified using silica gel column chromatography (TFA/Dichloromethane/ethyl acetate=1/5/40) to give compound 33 as a white solid (0.088 mmol). MS ESI m/e: 339 (M−H) 1H NMR (500 MHz) (DMSO-d6) δ 11.97 (1H, s); 7.31 (1H, t, J=10 Hz); 7.14 (2H, d, J=11 Hz); 6.99 (2H, m); 6.87 (3H, m); 5.22 (1H, s). 5.03 (2H, s); 3.75 (1H, m); 3.75 (3H, s); 2.44-2.53 (2H, m); 1.63 (3H, s); 1.62 (3H, s).

Workup

  1. temperaturewas refluxed for 16 h
  2. customAfter removing the solvent
  3. customthe residue was purified

Sources & evidence

ORD record
ord-bcc65f01e5a54c04b87867e55945f408
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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