Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glycine | HCID 750 | — |
| Reactant | (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal | HCID 107526 | — |
| Catalyst | Nickel | HCID 935 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 21427698 | HCID 21427698 | 73.2% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04032676 |
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| Source dataset | uspto-grants-1977_06 |
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| ORD ID | ord-583dd6406413492db71d2ed560d8a58a |
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| Source note | uspto-grants-1977_06 |
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