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Methanol → N-(2,3,4,5,6-pentahydroxy-hexyl)-L-(+)-citrulline

HRID 438007
Notes
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Reaction equation

HRID 438007 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[NH2:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH2:21])=[O:20].CO>[Ni].[Pd].O>[OH:4][CH:3]([CH:5]([OH:6])[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][OH:12])[CH2:2][NH:13][C@H:14]([C:22]([OH:24])=[O:23])[CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH2:21])=[O:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 887MethanolHCID 9750CitrullineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 53994813N-(2,3,4,5,6-pentahydroxy-hexyl)-L-(+)-citrulline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 23938Palladium
Catalyst
HCID 962WaterSolvent

Procedure

The product was made from D-glucose and L-(+)-citrulline using Raney nickel or palladium/activated carbon as a catalyst and heating for 2 hours to 50° C. and 4 hours to 70° C. A product was obtained which had a melting point of 176° C. and an RF -value of 0.7 (determined on DC-finished plates of silica gel G (Merck) with a transporting liquid made up of 50 parts by volume of methanol and 50 parts by volume of water).

Workup

  1. temperatureheating for 2 hours to 50° C. and 4 hours to 70° C
  2. customA product was obtained which

Sources & evidence

ORD record
ord-472cad92d8bf42c8b51cc60e4936cd3f
Source dataset
uspto-grants-1977_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04032676

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes