Benzyl [2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate → tert-Butyl {(4S)-5-[(aminoacetyl)amino]-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

HRID 269647Notes

Reaction equation

HRID 269647 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12]([NH:14][CH2:15][C@@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:13])C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][C@H:16]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:15][NH:14][C:12](=[O:13])[CH2:11][NH2:10])([CH3:27])([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 86624495Benzyl [2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate

Product 1

HCID 86624496tert-Butyl {(4S)-5-[(aminoacetyl)amino]-4-[(tert-butoxycarbonyl)amino]pentyl}carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation takes place in analogy to Example 81A from 105 mg (0.21 mmol) of benzyl[2-({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-2-oxoethyl]carbamate (Example 125A) in 50 ml of ethanol with the addition of 11 mg of palladium on activated carbon (10%). The product is reacted without further purification.

Workup

  1. customPreparation
  2. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-0d68d4ddee95466e87978181337225a4
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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