Dichloromethane → HCID 22033712, compound

HRID 1791877Notes

Reaction equation

HRID 1791877 reaction equation
[C:1]([NH:5][C:6]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22]CCC)=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])(=[O:4])[CH2:2][CH3:3].[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29].[CH2:32](Cl)Cl>>[C:26]([NH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][C:12]1[CH:13]=[CH:14][C:6]([NH:5][C:1]([CH:2]2[CH2:3][CH2:32]2)=[O:4])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])(=[O:30])[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 8855Butyryl chlorideHCID 22033669HCID 22033669, compound

Product 1

HCID 22033712HCID 22033712, compoundYield 31%

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(2-amino-phenoxy)-2-(cyclopropanecarbonyl-amino)-benzoic acid methyl ester (50.0 mg, 0.153 mmol, prepared according to EXAMPLE 2) and butyryl chloride (23.3 mg, 0.184 mmol) in CH2Cl2 (1.5 mL) was heated in a microwave oven at 110° C. for 10 minutes. The reaction mixture was allowed to reach room temperature and the solvent was removed by evaporation. The crude ester product was hydrolysed in methanol (2 mL) and 1M NaOH (1 mL) over night, acidified with 1M HCl and the product was isolated by filtration (18 mg, total yield: 31%).

Workup

  1. customto reach room temperature
  2. customthe solvent was removed by evaporation
  3. wait1M NaOH (1 mL) over night
  4. customthe product was isolated by filtration (18 mg, total yield: 31%)

Sources & evidence

ORD record
ord-0e623b6bc5f04c73904e0abc285f158f
Source dataset
uspto-grants-2006_07
Patent number
US07074831B2

Reaction notes

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