HCID 20773656, compound → HCID 178487675, compound

HRID 1815711Notes

Reaction equation

HRID 1815711 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[NH:12][C:13]([CH:15]1[CH2:17][CH2:16]1)=O)(=[O:3])[CH3:2].C(O[K])(C)(C)C>C(O)(C)(C)C>[CH:15]1([C:13]2[CH:2]=[C:1]([OH:3])[C:4]3[C:5](=[CH:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)[N:12]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 20773656HCID 20773656, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 178487675HCID 178487675, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Step 68b) A solution of product (5.35 g, 22.72 mmol) of step 1 example 376 {cyclopropanecarboxylic acid (2-acetyl-5-methoxy-phenyl)-amide} and tert-BuOK (5.45 g, 48.6 mmol) in tert-butanol (130 g) was refluxed for 6 h. The reaction mixture was cooled, poured into ice cold buffer and adjusted to pH 7, filtered. The solid collection was recrystallized from MeOH/Et2O to provide the product (1 g, 20%): 1H NMR (methanol-d4) δ ppm 0.96 (m, 2H), 1.15 (m, 2H), 1.94 (m, 1H), 3.87 (s, 3H), 5.86 (m, 1H), 6.93 (m, 2H), 8.04 (d, J=8.85 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured into ice cold buffer
  3. filtrationfiltered
  4. customThe solid collection
  5. customwas recrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-2eb411b71cd14d1280af81fba71e40e7
Source dataset
uspto-grants-2005_04
Patent number
US06878722B2

Reaction notes

Loading…