Trifluoroacetic acid → HCID 22623966, compound

HRID 279025Notes

Reaction equation

HRID 279025 reaction equation
C(O)(C(F)(F)F)=O.C([O:12][N:13]1[C:22](=[O:23])[C:21]2[CH:24]=[C:25]([O:40][CH3:41])[C:26]([N:27]3[CH2:31][CH2:30][CH:29]([NH:32]C(=O)OC(C)(C)C)[CH2:28]3)=[C:19]3[C:20]=2[C:15](=[CH:16][CH:17]=[CH:18]3)[C:14]1=[O:42])(C)(C)C>>[NH2:32][CH:29]1[CH2:30][CH2:31][N:27]([C:26]2[C:25]([O:40][CH3:41])=[CH:24][C:21]3[C:22](=[O:23])[N:13]([OH:12])[C:14](=[O:42])[C:15]4[C:20]=3[C:19]=2[CH:18]=[CH:17][CH:16]=4)[CH2:28]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86756250HCID 86756250, compound

Product 1

HCID 22623966HCID 22623966, compoundYield 15.3%

Procedure

Following the procedure from Example 62, TFA (1.0 mL) and [1-(2-tert-butyloxy-1,3-dioxo-2,3-dihydro-5-methoxy-1H-benzo[de]isoquinolin-6-yl)-pyrrolidin-3-yl]-carbamic acid, tert-butyl ester (0.2 g, 0.4 mmol, from Example N2) was stirred at room temperature overnight, concentrated, and the solid recrystallized from ethanol/ether to give 0.02 g of the title compound, mp 217-222° C.

Workup

  1. concentrationconcentrated
  2. customthe solid recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-7094657b7cf64874a689913dd21e92f9
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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