Trifluoroacetic acid → HCID 19593011, compound

HRID 613508Notes

Reaction equation

HRID 613508 reaction equation
C([O:5][C:6]([CH:8](C(OC(C)(C)C)=O)[C:9]1[C:18]2[C:13](=[C:14]([NH:19][C:20](=[O:29])[C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:6]([CH2:8][C:9]1[C:18]2[C:13](=[C:14]([NH:19][C:20](=[O:29])[C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19592403HCID 19592403, compound

Product 1

HCID 19593011HCID 19593011, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[bis(tert-butoxycarbonyl)methyl]-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (5.8 g) in dichloromethane (15 ml) was dropwise added trifluoroacetic acid (45 ml) under ice-cooling, and the mixture was stirred for 1 hour at ambient temperature. The mixture was concentrated in vacuo, and the residue was pulverized with diethyl ether to give 4-carboxymethyl-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (4.08 g).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-0e15ccf998ce4282a9cffedf8b4ca90c
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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