Trifluoroacetic acid → 2-amino-N-[(1R)-2-[4-benzyl-4-(N',N'-dimethylhydrazinocarbonyl)piperidin-1-yl]-1-((1H-indol-3-yl)methyl)-2-oxoethyl]-2-methylpropionamide

HRID 380665Notes

Reaction equation

HRID 380665 reaction equation
C(OC(=O)[NH:7][C:8]([C:11](=[O:45])[NH:12][CH:13]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[C:14]([N:16]1[CH2:21][CH2:20][C:19]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:22]([NH:24][N:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15])([CH3:10])[CH3:9])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C:8]([CH3:10])([CH3:9])[C:11]([NH:12][C@H:13]([CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)[C:14]([N:16]1[CH2:21][CH2:20][C:19]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:22]([NH:24][N:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15])=[O:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69019306(1-(2-(4-benzyl-4-(N',N'-dimethylhydrazinocarbonyl)piperidine-1-yl)-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamoyl)-1-methylethyl)carbamic acid tert-butyl ester

Product 1

HCID 98070912-amino-N-[(1R)-2-[4-benzyl-4-(N',N'-dimethylhydrazinocarbonyl)piperidin-1-yl]-1-((1H-indol-3-yl)methyl)-2-oxoethyl]-2-methylpropionamideYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(2-(4-benzyl-4-(N′,N′-dimethylhydrazinocarbonyl)piperidine-1-yl)-1-(1H-indol-3-ylmethyl)-2-oxoethylcarbamoyl)-1-methylethyl)carbamic acid tert-butyl ester (0.29 g, 0.46 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 0.25 g of 2-amino-N-[(1R)-2-[4-benzyl-4-(N′,N′-dimethylhydrazinocarbonyl)piperidin-1-yl]-1-((1H-indol-3-yl)methyl)-2-oxoethyl]-2-methylpropionamide as a white amorphous powder.

Workup

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

Sources & evidence

ORD record
ord-0656954c24a24a38ba6c4f611897b970
Source dataset
uspto-grants-2001_10
Patent number
US06303620B1

Reaction notes

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