3-Aminoquinoline → tert-butyl N-[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamate

HRID 2387422Notes

Reaction equation

HRID 2387422 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:24][C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C(OCC)(=O)C>[N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[C:25]([NH:24][C:10]([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:18][CH:19]=2)=[O:12])[CH:26]=1

Participants

5

Reactant 3

HCID 113753-AminoquinolineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 2736198N-[(1,1-Dimethylethoxy)carbonyl]-4-(trifluoromethyl)-D-phenylalanine

Product 1

HCID 67981032tert-butyl N-[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(trifluoromethyl)phenyl]propanoic acid XII (0.93 g, 2.79 mmol) and 3-aminoquinoline XIII (0.45 g, 3.10 mmol) in ethyl acetate (30 mL) was added DMT-MM (1.0 g, 3.63 mmol). After being stirred at r.t. overnight, the reaction was washed with water, 1 N HCl, aq. sat. NaHCO3, water and dried over Na2SO4. The solvent was removed under reduced pressure to afford tert-butyl N-[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamate (1.19 g, 2.59 mmol, 93% yield). 1H NMR (DMSO-d6) 1.31 (s, 9H), 2.95-3.15 (m, 1H), 3.22-3.27 (m, 1H), 4.46-4.52 (m, 1H), 7.36 (d, J=8 Hz, 1H), 7.62-7.68 (m, 4H), 7.67 (t, J=8 Hz, 1H), 7.83 (t, J=8 Hz, 1H), 8.13 (t, J=7 Hz, 2H), 8.99 (d, J=2 Hz, 1H), 9.24 (d, J=2 Hz, 1H), 11.18 (s, 1H); ESIMS found for C24H24N3O3F3 m/z 460 (M+H).

Workup

  1. washthe reaction was washed with water, 1 N HCl, aq. sat. NaHCO3, water
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-87f31027bade419bbb9bf0ddda113514
Source dataset
uspto-grants-2012_09
Patent number
US08268865B2

Reaction notes

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