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

HRID 269682Notes

Reaction equation

HRID 269682 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:23]([NH:25][C@H:26]([CH2:36][OH:37])[CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O: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][C@H:26]([CH2:36][OH:37])[CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:24])[NH2:10])=[O:17])([CH3:20])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 131727171Benzyl[(1S)-4-[(tert-butoxycarbonyl)amino]-1-({[(1S)-2-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)ethyl]amino}carbonyl)butyl]carbamate

Product 1

HCID 86619443N5-(tert-Butoxycarbonyl)-N-[(1S)-2-[(tert-butoxycarbonyl)amino]-1-(hydroxymethyl)ethyl]-L-ornithinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

40 mg of palladium on activated carbon (10%) are added to a mixture of 0.216 g (0.40 mmol) of the compound from Example 252A 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-78b71b2091d740ad9f2b7c7527e96b08
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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