Trifluoroacetic acid → HCID 58091437, compound

HRID 2045724Notes

Reaction equation

HRID 2045724 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([N:11]1[C:15]2[C:16]([O:24][C@H:25]3[CH2:29][N:28](C(OC(C)(C)C)=O)[C@H:27]([C:37]([O:39][CH3:40])=[O:38])[CH2:26]3)=[N:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:14]=2[C:13]([CH3:41])=[CH:12]1)[CH:9]=[CH2:10]>C(Cl)Cl.C1(C)C=CC=CC=1>[CH2:8]([N:11]1[C:15]2[C:16]([O:24][C@H:25]3[CH2:29][NH:28][C@H:27]([C:37]([O:39][CH3:40])=[O:38])[CH2:26]3)=[N:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:14]=2[C:13]([CH3:41])=[CH:12]1)[CH:9]=[CH2:10]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86649515HCID 86649515, compound

Product 1

HCID 58091437HCID 58091437, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (3 mL) was added to a solution of 1-tert-butyl 2-methyl (2S,4R)-4-[(3-allyl-1-methyl-3H-pyrrolo[2,3-c]quinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate (1.30 g, 2.79 mmol) in DCM (20 mL). The mixture was stirred for 4 h, then diluted with PhMe and concentrated under reduced pressure. The residue was taken up in EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated to give the title compound (1.02 g, 98%) as an oil that was used without further purification in subsequent steps. LCMS (ES+) m/z 366 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-caab8d0badfb490bb5da15195f2138e4
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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