HCID 57033160, compound → HCID 86756252, compound

HRID 279043Notes

Reaction equation

HRID 279043 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[C:15]([Cl:33])[C:16]3[C:17](=[O:32])[N:18]([O:28]CC=C)[C:19](=[O:27])[C:20]4[C:25]=3[C:24]=2[C:23]([Cl:26])=[CH:22][CH:21]=4)[CH2:9]1)(C)(C)C>FC(F)(F)C(O)=O>[ClH:26].[NH2:7][C@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[C:15]([Cl:33])[C:16]3[C:17](=[O:32])[N:18]([OH:28])[C:19](=[O:27])[C:20]4[C:25]=3[C:24]=2[C:23]([Cl:26])=[CH:22][CH:21]=4)[CH2:9]1

Participants

3

Reactant 1

HCID 57033160HCID 57033160, compound

Product 1

HCID 86756252HCID 86756252, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-[1-(2-allyloxy-4,7-dichloro-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester (0.3 g, 0.6 mmol, from Example K4) in 10 mL of trifluoroacetic acid was treated with boron tristrifluoroacetate (4 mL, 4.0 mmol, 1.0 M in trifluoroacetic acid). The reaction was stirred at room temperature for 2 hours and the solvent evaporated in vacuo. The residue was chased with dichloromethane and redissolved in methanol which was also evaporated. The residue was triturated with ether, the solid removed by filtration and dried in vacuo to give 0.27 g, mp 210-212° C.

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionredissolved in methanol which
  3. customwas also evaporated
  4. customThe residue was triturated with ether
  5. customthe solid removed by filtration
  6. customdried in vacuo
  7. customto give 0.27 g, mp 210-212° C.

Sources & evidence

ORD record
ord-117357a340304ede908a00b49ba2bc31
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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