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

HRID 269673Notes

Reaction equation

HRID 269673 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:23]([NH:25][CH2:26][CH2:27][C@H:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][OH:30])=[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>[Pd].C(O)C>[C:19]([O:18][C:16]([NH:15][CH2:14][CH2:13][CH2:12][C@@H:11]([C:23]([NH:25][CH2:26][CH2:27][C@H:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:29][OH:30])=[O:24])[NH2:10])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 1

HCID 131727168Benzyl{(1S)-4-[(tert-butoxycarbonyl)amino]-1-[({(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}amino)carbonyl]butyl}carbamate

Product 1

HCID 86619439N5-(tert-Butoxycarbonyl)-N-{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}-L-ornithinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

17 mg of palladium on activated carbon (10%) are added to a mixture of 0.088 g (0.16 mmol) of the compound from Example 238A in 10 ml of ethanol, and the mixture is then hydrogenated under atmospheric pressure for 12 h. The reaction mixture is filtered through kieselguhr, and the filtrate is concentrated in vacuo and dried under high vacuum. The crude product is reacted without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through kieselguhr
  2. concentrationthe filtrate is concentrated in vacuo
  3. customdried under high vacuum
  4. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-104f176c034a47a08122586e1a4db39e
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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