Triethylamine → 5'-(Cyclohexanecarbonyl-amino)-2'-chloro-biphenyl-4-carboxylic acid ethyl ester

HRID 1678487Notes

Reaction equation

HRID 1678487 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:14]=2[Cl:20])=[CH:9][CH:8]=1)=[O:6])[CH3:3].C(N(CC)CC)C.[CH:28]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([NH:19][C:34]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:35])[CH:16]=[CH:15][C:14]=2[Cl:20])=[CH:9][CH:8]=1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 673717565'-Amino-2'-chloro-biphenyl-4-carboxylic acid ethyl ester hydrochloride

Product 1

HCID 598223735'-(Cyclohexanecarbonyl-amino)-2'-chloro-biphenyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5′-amino-2′-chloro-biphenyl-4-carboxylic acid ethyl ester hydrochloride (521 mg), triethylamine (0.49 ml) and cyclohexanecarbonyl chloride (0.26 ml) in dry THF (25 ml) was stirred at 20 C for 18 h. The mixture was then evaporated and the residue partitioned between water and dichloromethane. The organic layer was washed with water, dried (MgSO4), filtered and evaporated under reduced pressure to give the product (714 mg) as a yellow oil.

Workup

  1. customThe mixture was then evaporated
  2. customthe residue partitioned between water and dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-037cb9190a3d44f1ac0d52fc84eb3ebb
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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