Trifluoroacetic acid → HCID 67195860, compound

HRID 2366958Notes

Reaction equation

HRID 2366958 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][CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[CH:25]=3)=[CH:18][CH:19]=2)[C@H:14]([NH:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])[CH2:13][C@@H:12]1[CH3:42])(=[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][CH2:27][C:28]([OH:30])=[O:29])[CH:25]=3)=[CH:18][CH:19]=2)[C@H:14]([NH:35][C:36]([O:38][CH:39]([CH3:41])[CH3:40])=[O:37])[CH2:13][C@@H:12]1[CH3:42])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 52934563HCID 52934563, compound

Product 1

HCID 67195860HCID 67195860, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoracetic acid (1 ml) was added to a solution of 1,1-dimethylethyl 3-{(cis)-4-[1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}propanoate (for a preparation see Example 91) (1.06 g, 2.19 mmol) in DCM (5 mL). The reaction mixture was allowed to stand at room temperature for 16 h then most of the solvent were removed in vacuo. The residue was co-evaporated twice with toluene then triturated with Et2O to give 3-{(cis)-4-[1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}propanoic acid trifluoroacetate (920 mg, 1.696 mmol, 78%) as an off-white solid.

Workup

  1. custommost of the solvent were removed in vacuo
  2. customthen triturated with Et2O

Sources & evidence

ORD record
ord-18817fe3af184207bb1d30a08e30b71d
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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