Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]butyl}carbamate → N5-(tert-Butoxycarbonyl)-N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}-L-ornithinamide

HRID 269610Notes

Reaction equation

HRID 269610 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:23]([NH:25][CH2:26][CH:27]([OH:37])[CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[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]([NH:15][CH2:14][CH2:13][CH2:12][C@@H:11]([C:23]([NH:25][CH2:26][CH:27]([OH:37])[CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:24])[NH2:10])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 1

HCID 131727147Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]butyl}carbamate

Product 1

HCID 86619422N5-(tert-Butoxycarbonyl)-N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}-L-ornithinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation takes place in analogy to Example 81A from 412 mg (0.76 mmol) of benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)carbonyl]butyl}carbamate (Example 80A) in 50 ml of ethanol with the addition of 41 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-4e0ee4f9bc8b49ac8eba7be265525cb3
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

Loading…