Water → 5-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637268Notes

Reaction equation

HRID 1637268 reaction equation
[NH2:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1.[C:20]([O:24][C:25]([NH:27][CH2:28][C:29](O)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21].ClC(Cl)CCCCCN=C=N.O>C(Cl)Cl>[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]([NH:1][CH:2]1[C:12]2[C:13]3[C:5](=[C:6]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:4][CH2:3]1)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 78288N-(tert-butoxycarbonyl)glycineHCID 101988185-Amino-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleHCID 71510291Dichlorohexylcarbodiimide

Product 1

HCID 193482985-[N-(N-t-butoxycarbonylglycyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 143.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (200 mg) of the compound obtained in Example 81 and N-t-butoxycarbonylglycine (170 mg) were suspended in methylene chloride (15 ml) and to the suspension was added dichlorohexylcarbodiimide (216 mg) under cooling with ice. The mixture was stirred for 1 hour at room temperature. To the reaction mixture was added water, followed by extraction 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 to yield the titled compound (470 mg) as a crude yellow solid. The compound was used in the subsequent reaction without further purification.

Workup

  1. temperatureunder cooling with ice
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dcc4a09ac9b04152b0917aa97b9017e5
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

Loading…