HCID 86667912, compound → HCID 67056938, compound

HRID 517516Notes

Reaction equation

HRID 517516 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C@@H:14]([CH2:19][NH:20][C:21](=[O:35])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:24][CH:23]=2)[C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].C(O)C>[CH3:34][O:33][CH2:32][CH2:31][O:30][CH2:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:20][CH2:19][C@H:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:15]([O:17][CH3:18])=[O:16])=[O:35])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 86667912HCID 86667912, compound

Product 1

HCID 67056938HCID 67056938, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

520 mg of 10 wt % palladium on carbon are added to a solution of 5.2 g (10.7 mmol) of methyl (S)-2-(4-benzylpiperazin-1-yl)-3-[4-(2-methoxyethoxymethoxy)-benzoylamino]propanoate (prepared as described in example 22-4) in 80 ml of ethanol previously degassed under a stream of nitrogen, and the mixture is placed under hydrogen at atmospheric pressure. After stirring for 18 h at ambient temperature, the reaction medium is filtered over celite. The filtrate is concentrated to give 3.8 g (90%) of methyl (S)-3-[4-(2-methoxyethoxy-methoxy)benzoylamino]-2-piperazin-1-ylpropanoate in the form of a colourless oil.

Workup

  1. custompreviously degassed under a stream of nitrogen
  2. filtrationthe reaction medium is filtered over celite
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-4b67fb9d62e242a7b1122edcca97c8c5
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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