Hydrazine → ethyl N-{4-[(5-amino-1H-indol-1-yl)methyl]benzoyl}phenylalaninate

HRID 2245515Notes

Reaction equation

HRID 2245515 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:35]=[CH:34][C:17]([C:18]([NH:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:19])=[CH:16][CH:15]=1)[CH:8]=[CH:7]2)([O-])=O.NN>C(O)C.C1COCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:19])=[CH:34][CH:35]=1)[CH:8]=[CH:7]2

Participants

6

Reactant 2

HCID 9321HydrazineHCID 68546120ethyl N-(4-[(5-nitro-1H-indol-1-yl)methyl]benzoyl)-L-phenylalaninate

Product 1

HCID 68548160ethyl N-{4-[(5-amino-1H-indol-1-yl)methyl]benzoyl}phenylalaninate

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A large excess of Raney® nickel was added in portions to a stirred solution of ethyl N-{4-[(5-nitro-1H-indol-1-yl)methyl]benzoyl}-L-phenylalaninate (2.36 g, 5 mmol), and hydrazine (1.2 mL, 38 mmol) in 100 mL of ethanol and 15 mL of THF. After stirring at room temperature for 2 h the catalyst was then removed by filtering through a short pad of Celite®521. The filtrate was concentrated to give ethyl N-{4-[(5-amino-1H-indol-1-yl)methyl]benzoyl}phenylalaninate as an off-white solid: MS (ESI) m/z 442.

Workup

  1. customwas then removed
  2. filtrationby filtering through a short pad of Celite®521
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-465f0819817042ccadecf9827d19f382
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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