Trifluoroacetic acid → HCID 54467012, compound

HRID 864607Notes

Reaction equation

HRID 864607 reaction equation
[C:1]([N:4]([C:13]1[CH:49]=[CH:48][C:16]([CH:17]=[CH:18][C:19]([NH:21][CH2:22][C:23]([N:25]([C:27]2[C:28]([Cl:47])=[C:29]([C:43]([Cl:46])=[CH:44][CH:45]=2)[CH2:30][O:31][C:32]2[CH:33]=[CH:34][CH:35]=[C:36]3[C:41]=2[N:40]=[C:39]([CH3:42])[CH:38]=[CH:37]3)[CH3:26])=[O:24])=[O:20])=[CH:15][CH:14]=1)[CH2:5][C:6]([O:8]C(C)(C)C)=[O:7])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([N:4]([C:13]1[CH:14]=[CH:15][C:16]([CH:17]=[CH:18][C:19]([NH:21][CH2:22][C:23]([N:25]([C:27]2[C:28]([Cl:47])=[C:29]([C:43]([Cl:46])=[CH:44][CH:45]=2)[CH2:30][O:31][C:32]2[CH:33]=[CH:34][CH:35]=[C:36]3[C:41]=2[N:40]=[C:39]([CH3:42])[CH:38]=[CH:37]3)[CH3:26])=[O:24])=[O:20])=[CH:48][CH:49]=1)[CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 54068740HCID 54068740, compound

Product 1

HCID 54467012HCID 54467012, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-[3-[N-[4-(N-acetyl-N-tert-butoxycarbonylmethylamino)cinnamoylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (143 mg) in dichloromethane (1.4 ml) was added trifluoroacetic acid (0.05 ml) at ambient temperature and the mixture was stirred at the same temperature. After 1 hour, to the solution was added trifluoroacetic acid (1 ml). After 5 hours the solvent was removed in vacuo to give 8-[3-[N-[4-(N-acetyl-N-carboxymethylamino)cinnamoylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (124 mg) as amorphous solid.

Workup

  1. customAfter 5 hours the solvent was removed in vacuo

Sources & evidence

ORD record
ord-895fcd8856ff43ba89fee726bf6c07ba
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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