Glycine → HCID 21427698, compound

HRID 438000Notes

Reaction equation

HRID 438000 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][CH2:14][C:15]([OH:17])=[O:16]>O.CO.[Ni]>[OH:4][CH:3]([CH:5]([OH:6])[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][OH:12])[CH2:2][NH:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 2

HCID 750GlycineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 21427698HCID 21427698, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 39.6 gm of D-glucose in 200 ml of water and 150 ml of methanol was added to a solution of 15 gm (0.2 mol) of glycine in 200 ml of water and 100 ml of methanol in an autoclave. Then, after the addition of 18.0 gm of Raney nickel, a hydrogenation was carried out in the autoclave with stirring at a pressure of 180 to 200 kg/cm2. The autoclave was heated in a progressive manner first for 2 hours to 50° C., subsequently for 2 hours to 70° C. and finally for 2 hours to 90° C. After separation of the catalyst by filtration and evaporation of the reaction solution in vacuum, the highly viscous residue obtained was allowed to stand for a few days. After crystallization had commenced the same was completed by crystallization from 100 ml of boiling methanol. 35 gm (73% of theory) of N-(2,3,4,5,6-pentahydroxy-hexyl)-glycine having a melting point of 172° to 177° C. (decomposition) were obtained. An analytically pure sample recrystallized from water/ 2-propanol melted at 175° to 180° C. with decomposition.

Workup

  1. temperatureThe autoclave was heated in a progressive manner first for 2 hours to 50° C., subsequently for 2 hours to 70° C. and finally for 2 hours to 90° C
  2. customAfter separation of the catalyst
  3. filtrationby filtration and evaporation of the reaction solution in vacuum
  4. customthe highly viscous residue obtained
  5. waitto stand for a few days
  6. customAfter crystallization
  7. customsame was completed by crystallization from 100 ml of boiling methanol

Sources & evidence

ORD record
ord-583dd6406413492db71d2ed560d8a58a
Source dataset
uspto-grants-1977_06
Patent number
US04032676

Reaction notes

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