Trifluoroacetic acid → 5-(N-glycylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637269Notes

Reaction equation

HRID 1637269 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][CH:13]1[C:23]2[C:24]3[C:16](=[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:18][C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14]1)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:8][CH2:9][C:10]([NH:12][CH:13]1[C:23]2[C:24]3[C:16](=[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:18][C:19]=3[CH:20]=[CH:21][CH:22]=2)[CH2:15][CH2:14]1)=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 193482985-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

Product 1

HCID 193483575-(N-glycylamino)-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (470 mg) of the crude compound obtained in Example 126 was suspended in methylene chloride (4 ml) and to the suspension was added trifluoroacetic acid (4 ml). The mixture was stirred for 1 hour at room temperature. The reaction mixture was made basic with saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1) to yield 100 mg (41%) of the titled compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-ethyl acetate/methanol=9:1)

Sources & evidence

ORD record
ord-3cf1cf431d5b482eb804bdc75085585f
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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