HCID 21821191, compound → Ammonia

HRID 917824Notes

Reaction equation

HRID 917824 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][N:8]([C@@H:10]2[O:32][C@H:31]([CH2:33][O:34]C(=O)C3C=CC=CC=3)[C@@H:21]([O:22]C(=O)C3C=CC=CC=3)[C@H:11]2[O:12]C(=O)C2C=CC=CC=2)[N:9]=1)=O.COC(C1[N:48]=N[N:50]([C@@H:52]2[O:74][C@H](COC(=O)C3C=CC=CC=3)[C@@H](OC(=O)C3C=CC=CC=3)[C@H]2OC(=O)C2C=CC=CC=2)C=1)=O.COC([C:89]1[N:93]([C@@H:94]2[O:116][C@H:115]([CH2:117][O:118]C(=O)C3C=CC=CC=3)[C@@H:105]([O:106]C(=O)C3C=CC=CC=3)[C@H:95]2[O:96]C(=O)C2C=CC=CC=2)[N:92]=[N:91][CH:90]=1)=O>>[NH3:7].[C@@H:10]1([N:8]2[N:9]=[C:5]([C:3]([NH2:48])=[O:2])[CH:6]=[N:7]2)[O:32][C@H:31]([CH2:33][OH:34])[C@@H:21]([OH:22])[C@H:11]1[OH:12].[C@@H:94]1([N:93]2[CH:89]=[C:90]([C:52]([NH2:50])=[O:74])[N:91]=[N:92]2)[O:116][C@H:115]([CH2:117][OH:118])[C@@H:105]([OH:106])[C@H:95]1[OH:96]

Participants

6

Reactant 3

HCID 21821191HCID 21821191, compoundHCID 21821199HCID 21821199, compoundHCID 21825581HCID 21825581, compound

Product 3

HCID 222AmmoniaHCID 21821194HCID 21821194, compoundHCID 21825595HCID 21825595, compound

Procedure

Fusion of methyl 1,2,3-triazole-4-carboxylate prepared as in F. P. Woerner et al., Chem. Ber., 103, 1908 (1970) with 1-0-acetyl-2,3,5-tri-0-benzoyl-β-D-ribofuranose in the presence of an acidic catalyst provides a mixture of 2-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole-5-carboxylic acid methyl ester (1) and 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole-4caboxylic acid methyl ester (2) in respective ratio of about 2:1, together with a small fraction of 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,3-triazole-5-carboxylic acid methyl ester. The particular carboxylic acid ester group of the starting base is not critical, as its alkoxy component is split off in the following step of conversion to the bioactive carboxamide. Again, for ease of workup, lower carboxylic acid esters such as carbomethoxy or carboethoxy groups are preferred. Treatment of 1 and 2 with methanolic ammonia provides 2-β-ribofuranosyl-1,2,3-triazole-4-carboxamide (4) and 1-β-D-ribofuranosyl-1,2,3-triazole-4-carboxamide (5). The isomeric 1-β-O-ribofuranosyl-1,2,3 -triazole-5-carboxamide may be similarly obtained from 3. If desired, glycosyl hydroxyl blocking groups may be removed before conversion to the carboxamide. For example, compound 1 may be debenzoylated by reaction with sodium methoxide is methanol.

Workup

  1. customas its alkoxy component is split off in the following step of conversion to the bioactive carboxamide

Sources & evidence

ORD record
ord-c8523096e042484a8e20af46f45de2e6
Source dataset
uspto-grants-1976_07
Patent number
US03968103

Reaction notes

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