Trifluoroacetic acid → 1-(2-amino-3-(1H-indol-3-yl)propionyl)-4-benzylpiperidine-4-carboxylic acid N',N'-dimethylhydrazide

HRID 380663Notes

Reaction equation

HRID 380663 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:17]([NH:19][N:20]([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:22][N:20]([CH3:21])[NH:19][C:17]([C:14]1([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][CH2:12][N:11]([C:9](=[O:10])[CH:8]([NH2:7])[CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)[CH2:16][CH2:15]1)=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20694720(2-(4-benzyl-4-(N',N'-dimethylhydrazinocarbonyl)piperidine-1-yl)-1-(1H-indole-3-ylmethyl)-2-oxoethyl)carbamic acid tert-butyl ester

Product 1

HCID 206947011-(2-amino-3-(1H-indol-3-yl)propionyl)-4-benzylpiperidine-4-carboxylic acid N',N'-dimethylhydrazideYield 192.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-(4-benzyl-4-(N′,N′-dimethylhydrazinocarbonyl)piperidine-1-yl)-1-(1H-indole-3-ylmethyl)-2-oxoethyl)carbamic acid tert-butyl ester (0.40 g, 0.73 mmol) in methylene chloride (3 ml) at 0° C. was added trifluoroacetic acid (3 ml) and the mixture was stirred for 30 min. The mixture was quenched with ethanol (20 ml), concentrated in vacuo and stripped three times with methylene chloride to give 0.63 g of 1-(2-amino-3-(1H-indol-3-yl)propionyl)-4-benzylpiperidine-4-carboxylic acid N′,N′-dimethylhydrazide as a colorless oil.

Workup

  1. customThe mixture was quenched with ethanol (20 ml)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f16fab6ced24b3fb1d3a05ec21c993a
Source dataset
uspto-grants-2001_10
Patent number
US06303620B1

Reaction notes

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