Ammonia → (2R,3R,4S,5R)-2-(2-amino-5,6-dichloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

HRID 2255937Notes

Reaction equation

HRID 2255937 reaction equation
Cl[C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1.[NH3:31]>CO>[NH2:31][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:25]=[C:26]([Cl:30])[C:27]([Cl:29])=[CH:28][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 466019[(2R,3R,4R,5R)-3,4-diacetoxy-5-(2,5,6-trichlorobenzimidazol-1-yl)tetrahydrofuran-2-yl]methyl acetate

Product 1

HCID 466018(2R,3R,4S,5R)-2-(2-amino-5,6-dichloro-benzimidazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5,6-Trichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)benzimidazole (42, 0.48 g; l mmole) was dissolved in dry MeOH (10 ml). Liq. NH3 (10 ml) was added and the mixture heated in a steel bomb at 100° C. for 2 hr. This mixture was stirred at room temperature for 24 hr. Excess NH3 was allowed to evaporate and the solution evaporated to dryness, absorbed onto silica gel (2 g), and chromatographed on a silica gel column using silica gel (20 g; 60-200 mesh). Bution of the column with CH2Cl2 :CH3OH (96:4) gave the desired compound 44 as the major nucleoside. Evaporation of the solvent and crystallization of the residue from EtOH gave 44 (0.62 g; yield 6.06%). top. 145° C.; UV lmax. (MeOH): 259 (7941) and 301 (8348) nm; lmax (pH1): 215 (26000) and 292 (7520) nm; lmax (pH11): 257 (7967) and 298 (7107) nm. 1H NMR(DMSO- d6): d 8.70 (s, 1H, C7 -H, 8.28(s,1H, C4 -H), 7.90 (bs,2H, D2O exchangeable, NH2), 6.75(d,C1'H,J1,2 =4.5 Hz) and the rest of the sugar protons.

Workup

  1. customto evaporate
  2. customthe solution evaporated to dryness
  3. customabsorbed onto silica gel (2 g)
  4. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-4910237c56c84da0962de8fb38e6026d
Source dataset
uspto-grants-1997_08
Patent number
US05654283

Reaction notes

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