HCID 92268424, compound → (6R,9R,12R)-6,9-Dibenzyl-12-isobutyl-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oic acid

HRID 12080Notes

Reaction equation

HRID 12080 reaction equation
[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@@H:2]([C:10]([NH:12][C@@H:13]([C:21]([NH:23][C@@H:24]([C:29]([O:31]CC1C=CC=CC=1)=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[NH:1]([C:39]([O:41][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:40])[C@@H:2]([C:10]([NH:12][C@@H:13]([C:21]([NH:23][C@@H:24]([C:29]([OH:31])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:22])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 92268424HCID 92268424, compound

Product 1

HCID 68223108(6R,9R,12R)-6,9-Dibenzyl-12-isobutyl-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flask flushed with nitrogen was added wet palladium on carbon (1.8 g) and a solution of Boc-D-Phe-D-Phe-D-Leu-OBn, intermediate 1-5 (11.1 g, 18.05 mmol) in methanol (50 μL). The mixture was stirred under a hydrogen balloon overnight. After filtration through celite, methanol was evaporated under reduced pressure. The residue was dissolved in acetone (20 mL) and slowly added to 500 mL water with 25 mL of 1N HCl under vigorous stirring. Pure product Boc-D-Phe-D-Phe-D-Leu-OH, intermediate 1-6 was obtained by filtration 9.4 g (99%). LC-MS: m/z=526 (M+H).

Workup

  1. customIn a flask flushed with nitrogen
  2. additionwas added wet palladium on carbon (1.8 g)
  3. filtrationAfter filtration through celite, methanol
  4. customwas evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in acetone (20 mL)
  6. additionslowly added to 500 mL water with 25 mL of 1N HCl under vigorous stirring

Sources & evidence

ORD record
ord-f8ba92078b904485847e2987af2a83d5
Source dataset
uspto-grants-2010_06
Patent number
US07727963B2

Reaction notes

Loading…