4-(Trifluoromethoxy)benzoyl Chloride → [Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl ester

HRID 545336Notes

Reaction equation

HRID 545336 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][NH:6][CH:7]1[CH2:9][CH2:8]1)[CH3:2].[F:11][C:12]([F:24])([F:23])[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl.C(=O)([O-])O.[Na+]>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][N:6]([CH:7]1[CH2:9][CH2:8]1)[C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([O:13][C:12]([F:11])([F:23])[F:24])=[CH:15][CH:16]=1)[CH3:2]

Participants

5

Reactant 2

HCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 22476174Glycine, N-cyclopropyl-, ethyl ester

Product 1

HCID 67133328[Cyclopropyl-(4-trifluoromethoxy-benzoyl)-amino]-acetic acid ethyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a vigorously stirred solution of 4.9 g (34 mmol) of cyclopropylamino-acetic acid ethyl ester in 50 ml of CH2Cl2 and 25 ml of saturated sodium hydrogen carbonate was added a solution of 8.4 g (37 mmol) of 4-(trifluoromethoxy)benzoyl chloride in 10 ml of CH2Cl2 and the reaction stirred for 1 h. The organic phase was then separated, dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 1:9 to 3:7] afforded 8.9 g (80%) of the title compound as a colorless oil. MS: 332.1 (MH+).

Workup

  1. customThe organic phase was then separated
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customPurification by flash column chromatography [n-heptane/EtOAc 1:9 to 3:7]

Sources & evidence

ORD record
ord-f28b5a8b40a249728586f15b19888ff6
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

Loading…