Hydrochloric Acid → HCID 18336821, compound

HRID 2297681Notes

Reaction equation

HRID 2297681 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]#[CH:15])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2Cl)(=[O:3])[CH3:2].[OH:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1.Cl>CN(C=O)C>[C:1]([O:4][C@@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([C:14]#[CH:15])[O:7][C@H:6]1[N:16]1[CH:24]=[N:23][C:22]2[C:17]1=[N:18][CH:19]=[N:20][C:21]=2[O:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[N:28]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 86588185HCID 86588185, compound

Product 1

HCID 18336821HCID 18336821, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R,3R,4R,5R)-4-(acetyloxy)-2-(6-chloro-9H-purin-9-yl)-5-ethynyltetrahydrofuran-3-yl acetate (104 mg) was treated with 1-hydroxybenzotriazole (136 mg) in dry DMF (3 ml) for 45 h at 22° C. The mixture was poured into ice cooled 1M hydrochloric acid (50 ml) and extracted with dichloromethane (3×25 ml); the organic layers were washed with water (20 ml) and saturated aqueous sodium bicarbonate (20 ml), dried (MgSO4) and evaporated in vacuo to give a colourless gum (148 mg).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with dichloromethane (3×25 ml)
  3. washthe organic layers were washed with water (20 ml) and saturated aqueous sodium bicarbonate (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-85508904a6604d3ba71721bb32c33cb8
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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