HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-valine (R)-alpha-methoxymethylbenzylamide → alpha-L-aspartyl-D-valine (R)-alpha-methoxymethylbenzylamide

HRID 774
Notes
Print preview

Reaction equation

HRID 774 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12](=[O:43])[C@@H:13]([CH:40]([CH3:42])[CH3:41])[NH:14][C:15](=[O:39])[C@H:16]([CH:28](CC1C=CC=CC=1)[C:29](=[O:31])[OH:30])[NH:17]C(OCC1C=CC=CC=1)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.O.[Pd].[C]>[CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12](=[O:43])[C@@H:13]([CH:40]([CH3:41])[CH3:42])[NH:14][C:15](=[O:39])[C@H:16]([CH2:28][C:29](=[O:30])[OH:31])[NH2:17])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 53886295N-benzyloxycarbonyl-beta-benzyl-L-aspartyl-D-valine (R)-alpha-methoxymethylbenzylamide

Product 1

HCID 11793217alpha-L-aspartyl-D-valine (R)-alpha-methoxymethylbenzylamideYield 70.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962
Water
Solvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 6.20 g (10.5 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide in 200 ml of methanol and 50 ml of water was added 1.50 g of 10% Pd-carbon (water content 50%). The mixture was reduced under hydrogen under heat at 40° C. The catalyst was removed by filtration, and the resulting filtrate was concentrated under reduced pressure to 15 ml. The crystal thus precipitated was removed by filtration and dried to obtain 2.69 g (7.36 mmols, 70.0% ) of α-L-aspartyl-D-valine (R)-α-methoxymethylbenzylamide.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe resulting filtrate was concentrated under reduced pressure to 15 ml
  3. customThe crystal thus precipitated
  4. customwas removed by filtration
  5. customdried

Sources & evidence

ORD record
ord-1b033c485fa54b2cb55a6e97a581a99c
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723165

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes