Trifluoroacetic acid → HCID 67203682, compound

HRID 2366950Notes

Reaction equation

HRID 2366950 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[N:22]=[CH:23][N:24]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[CH:25]=3)=[CH:18][CH:19]=2)[C@H:14]([NH:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH2:13][C@@H:12]1[CH3:41])(=[O:10])[CH3:9]>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[N:22]=[CH:23][N:24]([CH2:26][C:27]([OH:29])=[O:28])[CH:25]=3)=[CH:18][CH:19]=2)[C@H:14]([NH:34][C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH2:13][C@@H:12]1[CH3:41])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86669276HCID 86669276, compound

Product 1

HCID 67203682HCID 67203682, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoracetic acid (1 mL) was added at room temperature to a solution of 1,1-dimethylethyl {(cis)-4-[1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}acetate (for a preparation see Example 91) (1.26 g, 2.68 mmol) in DCM (5 mL). The reaction mixture was allowed to stand at room temperature for 16 h then concentrated in vacuo. The residue was co-evaporated twice with toluene then triturated with Et2O to give {4-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}acetic acid trifluoroacetate (1.19 g, 2.252 mmol, 84%) as an off-white solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customthen triturated with Et2O

Sources & evidence

ORD record
ord-c48134f3f4164d3b9b14ab60c4a7a4ed
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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