HCID 71115295, compound → HCID 86675027, compound

HRID 2202197Notes

Reaction equation

HRID 2202197 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C@@H:14]([CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([O:23][C:21]([NH:20][CH2:19][C@H:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:15]([O:17][CH3:18])=[O:16])=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 71115295HCID 71115295, compound

Product 1

HCID 86675027HCID 86675027, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 g (25% by weight) of palladium-on-carbon at 10% are added to a solution of 8 g (21 mmol) of methyl(S)-2-(4-benzylpiperazin-1-yl)-3-tert-butoxycarbonylaminopropanoate (prepared as described in example 17.4) in 120 ml of ethanol, degassed beforehand under a nitrogen stream. The reaction medium is then placed under a hydrogen atmospheric pressure for 24 h and then filtered through celite and thoroughly rinsed with dichloromethane. After concentration under vacuum, 6.1 g (100%) of methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate are obtained.

Workup

  1. customdegassed
  2. customfor 24 h
  3. filtrationfiltered through celite and
  4. washthoroughly rinsed with dichloromethane
  5. concentrationAfter concentration under vacuum, 6.1 g (100%) of methyl (S)-3-tert-butoxycarbonylamino-2-piperazin-1-ylpropanoate
  6. customare obtained

Sources & evidence

ORD record
ord-3c27f9e378534d9f94f0473884fd7f3d
Source dataset
uspto-grants-2016_06
Patent number
US09365529B2

Reaction notes

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