Water → 4-[4-(Cyclopropanecarbonylamino)cyclohexyloxy]benzoic acid ethyl ester

HRID 555379Notes

Reaction equation

HRID 555379 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1.O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:23]([CH:20]3[CH2:22][CH2:21]3)=[O:24])[CH2:14][CH2:13]2)=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 167561694-(4-Aminocyclohexyloxy)benzoic acid ethyl ester

Product 1

HCID 666302994-[4-(Cyclopropanecarbonylamino)cyclohexyloxy]benzoic acid ethyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-aminocyclohexyloxy)benzoic acid ethyl ester (4.15 g, 15.76 mmol) in DCM (40 mL) at 0° C. was added TEA (1.6 g, 15.7 mmol) followed by cyclopropane carbonyl chloride (1.98 g, 18.9 mmol) over a period of 1 hr. Stirring was continued at 0-5° C. for 2 h. Water (40 mL) was then added and extracted with EtOAc. The organic layer was washed with 2N HCl, satd.NaHCO3 and brine solution. It was dried and concentrated under vacuum affording 4.75 g (91%) of 4-[4-(cyclopropanecarbonyl-amino)-cyclohexyloxy]-benzoic acid ethyl ester as an oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with 2N HCl
  3. customIt was dried
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-60180c7fb27741359338b59280b48d85
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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