Benzyl {(1S)-1-[({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-[(tert-butoxycarbonyl)amino]butyl}carbamate → Tert-butyl[(4s)-4-amino-5-({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-5-oxopentyl]carbamate

HRID 269641Notes

Reaction equation

HRID 269641 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:23]([NH:25][CH2:26][C@@H:27]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:24])[CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C1C=CC=CC=1>C(O)C.[Pd]>[C:19]([O:18][C:16](=[O:17])[NH:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH2:10])[C:23]([NH:25][CH2:26][C@@H:27]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:28][CH2:29][CH2:30][NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])=[O:24])([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 86624497Benzyl {(1S)-1-[({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-[(tert-butoxycarbonyl)amino]butyl}carbamate

Product 1

HCID 86624530Tert-butyl[(4s)-4-amino-5-({(2s)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)-5-oxopentyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation takes place in analogy to Example 81A from 132 mg (0.20 mmol) of benzyl{(1S)-1-[({(2S)-2,5-bis[(tert-butoxycarbonyl)amino]pentyl}amino)carbonyl]-4-[(tert-butoxycarbonyl)amino]butyl}carbamate (Example 119A) in 50 ml of ethanol with the addition of 13 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-d298cf61992643f98bff20aa0711c269
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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