Hydrochloric Acid → HCID 86739743, compound

HRID 1633271Notes

Reaction equation

HRID 1633271 reaction equation
[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:27][C@H:26]([C:28]([O:30][CH3:31])=[O:29])[C@@H:25]([N:32]=[N+:33]=[N-:34])[C@H:20]1[O:21]C(=O)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>[OH-].[Na+]>[C:1]([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:27][C@H:26]([C:28]([O:30][CH3:31])=[O:29])[C@@H:25]([N:32]=[N+:33]=[N-:34])[C@H:20]1[OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54278939HCID 54278939, compound

Product 1

HCID 86739743HCID 86739743, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 1-(6-benzoylamino-9H-purin-9-yl)-2-O-acetyl-3-azido-1,3-dideoxy-β-D-ribofuranuronate (1.10 g) prepared in Preparation 4 in 0.5N aqueous sodium hydroxide (25 ml) was stirred for 30 minutes. The solution was adjusted to pH 1 with 10% hydrochloric acid and extracted with ethyl acetate. After the extract was washed with brine, a solution of diazomethane in diethyl ether was dropped thereto until the yellow color was not disappeared. The solution was dried over magnesium sulfate and evaporated to dryness. The residue was triturated in diethyl ether to give methyl 1-(6-benzoylamino-9H-purin-9-yl)-3-azido-1,3-dideoxy-β-D-ribofuranuronate (433 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the extract was washed with brine
  3. additiona solution of diazomethane in diethyl ether was dropped
  4. dry with materialThe solution was dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-47f61b4c563041bc8a358a049c5bae67
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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