Acetic Acid → alpha-L-aspartyl-D-threonine (S)-alpha-ethylbenzylamide

HRID 768

Reaction equation

HRID 768 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11](=[O:49])[C@@H:12]([C@H:39]([CH3:48])[O:40]CC1C=CC=CC=1)[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].C(O)(=O)C>CO.[Pd].[C]>[CH2:1]([C@H:3]([NH:10][C:11](=[O:49])[C@@H:12]([C@H:39]([CH3:48])[OH: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 2

HCID 176Acetic AcidHCID 54057312N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-O-benzyl-D-threonine (S)-alpha-ethylbenzylamide

Product 1

HCID 22882903alpha-L-aspartyl-D-threonine (S)-alpha-ethylbenzylamideYield 57.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5.30 g (8.0 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-O-benzyl-D-threonine (S)-α-ethylbenzylamide in 150 ml of methanol were added 1.0 ml of acetic acid and 3.0 g of 5% Pd-carbon (water content 50%), and the mixture was reduced under hydrogen overnight at room temperature and then at 50° C. for 3 hours. The catalyst was removed by filtration, the resulting filtrate was concentrated under reduced pressure, and the residue was crystallized from water to obtain 1.60 g (4.6 mmols) of α-L-aspartyl-D-threonine (S)-α-ethylbenzylamide.

Workup

  1. waitat 50° C. for 3 hours
  2. customThe catalyst was removed by filtration
  3. concentrationthe resulting filtrate was concentrated under reduced pressure
  4. customthe residue was crystallized from water

Sources & evidence

ORD record
ord-ec57be9eb3044d5884323695460dbccf
Source dataset
uspto-grants-1998_03
Patent number
US05723165

Linked notes

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