N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamide → alpha-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamide

HRID 770

Reaction equation

HRID 770 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11](=[O:43])[C@@H:12]([C@@H:39]([CH2:41][CH3:42])[CH3:40])[NH:13][C:14](=[O:38])[C@H:15]([CH:27](CC1C=CC=CC=1)[C:28](=[O:30])[OH:29])[NH:16]C(OCC1C=CC=CC=1)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]>CO.O.[Pd].[C]>[CH2:1]([C@H:3]([NH:10][C:11](=[O:43])[C@@H:12]([C@@H:39]([CH2:41][CH3:42])[CH3:40])[NH:13][C:14](=[O:38])[C@H:15]([CH2:27][C:28](=[O:29])[OH:30])[NH2:16])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 1

HCID 53679369N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamide

Product 1

HCID 54262672alpha-L-aspartyl-D-isoleucine (S)-alpha-ethylbenzylamideYield 72.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2.81 g (4.7 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide in 150 ml of methanol and 50 ml of water was added 2.0 g of 10% Pd-carbon (water content 50%). The mixture was reduced under hydrogen at room temperature for 5 hours. The catalyst was removed by filtration, and the resulting filtrate was concentrated under reduced pressure to be 20 ml. The crystals thus precipitated were taken out by filtration and dried to obtain 1.22 g (3.4 mmols) of α-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. customThe crystals thus precipitated
  4. filtrationwere taken out by filtration
  5. customdried

Sources & evidence

ORD record
ord-b4a1a9f06c874053b3ad0f85aaa15884
Source dataset
uspto-grants-1998_03
Patent number
US05723165

Linked notes

Loading…