Trifluoroacetic acid → Methyl 3-[2-(2,6-dichlorophenyl)quinolin-6-yl]alaninate

HRID 1869781Notes

Reaction equation

HRID 1869781 reaction equation
C(OC([NH:8][CH:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])[CH:19]=[CH:18]2)[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[C:20]([C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])[CH:19]=[CH:18]2)[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11248518methyl N-(tert-butoxycarbonyl)-3-[2-(2,6-dichlorophenyl)-6-quinolyl]alaninate

Product 1

HCID 24755559Methyl 3-[2-(2,6-dichlorophenyl)quinolin-6-yl]alaninateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.15 g of methyl 2-[(tert-butoxycarbonyl)amino]-3-[2-(2,6-dichlorophenyl)-6-quinolinyl]propanoate 6 are solubilized in CH2Cl2 (50 ml). TFA (50 ml) is added at 0° C., and the mixture is stirred at RT for 6 h. After evaporation of the solvent, the residue is triturated in diethyl ether and cooled at 5° C. The solid product 33 is obtained by filtration.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is triturated in diethyl ether
  3. temperaturecooled at 5° C

Sources & evidence

ORD record
ord-5d62fed8fc4c49e08d5aed04b5ea873c
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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