Ethyl chloroformate → HCID 24955673, compound

HRID 1967576Notes

Reaction equation

HRID 1967576 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:23]([CH2:25][CH3:26])[CH3:24])[CH:16]=2)=[C:9]([Cl:27])[CH:8]=1)[CH3:2].Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:23]([CH2:25][CH3:26])[CH3:24])[CH:16]=2)=[C:9]([Cl:27])[CH:8]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:2]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 68557314HCID 68557314, compound

Product 1

HCID 24955673HCID 24955673, compoundYield 76%

Procedure

[4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenylamino]-acetic acid ethyl ester (0.9 g, 2.1 mmol) was stirred with ethyl chloroformate (8 mL) at reflux temperature for 16 hrs. From the reaction mixture ethyl chloroformate was evaporated under reduced pressure and the residue was taken up in ethyl acetate, washed with H2O, brine and dried over sodium sulphate, filtered and concentrated to give {[4-(3-sec-butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonyl-amino}-acetic acid ethyl ester. (0.8 g, 76% yield)

Workup

  1. temperatureat reflux temperature for 16 hrs
  2. customFrom the reaction mixture ethyl chloroformate was evaporated under reduced pressure
  3. washwashed with H2O, brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f22626fd50e547119fa00b2be16465ff
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

Loading…