Chloroform → HCID 58276466, compound

HRID 70318Notes

Reaction equation

HRID 70318 reaction equation
[NH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)[CH:11]=2)=[CH:6][CH:5]=1)=[O:3].FC(F)(F)C(O)=O.C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>C(Cl)Cl>[NH2:18][CH2:17][CH2:16][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:2]([NH2:1])=[O:3])=[CH:5][CH:6]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 58276276HCID 58276276, compound

Product 1

HCID 58276466HCID 58276466, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl {2-[4′-(aminocarbonyl)-3-biphenylyl]ethyl}-carbamate (1.81 g, 0.005 mol) in CH2Cl2 (50 mL) at room temperature was added trifluoroacetic acid (15 mL) in one portion. After 1 hr the mixture was cooled in an ice bath and 1M K2CO3 (200 mL) and chloroform were added. The aqueous phase was extracted several times with mixtures of ethyl acetate, dichloromethane and chloroform. Residual solids were collected by filtration, affording the title compound as a white solid; LC/MS (method A) 1.04 min; m/z 241 (M+H). Combined organic extracts were dried over Na2SO4 and concentrated in vacuo affording an additional batch of the title compound (combined with the solid collected above). This product was used without further purification.

Workup

  1. temperatureAfter 1 hr the mixture was cooled in an ice bath
  2. extractionThe aqueous phase was extracted several times with mixtures of ethyl acetate, dichloromethane and chloroform
  3. filtrationResidual solids were collected by filtration

Sources & evidence

ORD record
ord-b2ecfdae644b409ebfda62fb6db5a047
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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