Hydrazine → HCID 67497053, compound

HRID 1628306Notes

Reaction equation

HRID 1628306 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:9]([N:11]1[C:19]2[CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:16]=[C:15]([C:26]([O:28]C)=O)[C:14]=2[CH2:13][CH2:12]1)=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:37][NH2:38]>CCO>[C:1]([O:5][C:6]([C@@H:8]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:9]([N:11]1[C:19]2[CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH:16]=[C:15]([C:26]([NH:37][NH2:38])=[O:28])[C:14]=2[CH2:13][CH2:12]1)=[O:10])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68759365HCID 68759365, compound

Product 1

HCID 67497053HCID 67497053, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (S)-methyl 1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylate 58.A (339 mg, 0.68 mmol, prepared as in example 54.1) was added 4 mL EtOH and hydrazine (0.3 mL, 0.96 mmol). The reaction was refluxed overnight and concentrated. Silica gel purification afforded 250 mg (74%) product 58.B.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. concentrationconcentrated
  3. customSilica gel purification

Sources & evidence

ORD record
ord-9db94e85b4de436aa9e20802b0ac2c51
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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