Ethanesulfonic acid → HCID 14855154, compound

HRID 330586

Reaction equation

HRID 330586 reaction equation
C([N:4]1[C:12]([Cl:13])=[C:11]2[C:7](=[N:8][CH:9]=[N:10]2)[N:6]=[C:5]1[NH:14][C:15](=[O:17])[CH3:16])(=O)C.C(O[CH2:22][O:23][CH:24]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[CH2:25][O:26][C:27](=[O:29])[CH3:28])(=O)C.C(S(O)(=O)=O)C>ClCCl>[C:32]([O:31][CH2:30][CH:24]([O:23][CH2:22][N:8]1[CH:9]=[N:10][C:11]2[C:7]1=[N:6][C:5]([NH:14][C:15](=[O:17])[CH3:16])=[N:4][C:12]=2[Cl:13])[CH2:25][O:26][C:27](=[O:29])[CH3:28])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 11668Ethanesulfonic acidHCID 97948881,3-Propanediol, 2-((acetyloxy)methoxy)-, 1,3-diacetateHCID 178474411HCID 178474411, compound

Product 1

HCID 14855154HCID 14855154, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask (10 ml) was charged with N-acetyl-2-acetamido-6-chloropurine (2.0 g, 7.9 mmoles), 1,3-diacetoxy-2-propoxymethyl acetate (2.7 g, 10.9 mmoles), and ethanesulfonic acid (63 mg). The mixture was heated in an oil bath maintained at 130° and a vacuum was applied. Thin layer chromatography showed no heterocyclic starting material after 1.5 hours and heating was discontinued. The mixture was dissolved in dichloromethane (50 ml) and filtered through Celite. The filtrate was evaporated to a residue and chromatographed on silica gel using dichloromethane/methanol (98:2) as the eluant. The product-containing fractions were combined and evaporated to give 0.75 g of pure product, m.p. 139°-140°.

Workup

  1. temperatureThe mixture was heated in an oil bath
  2. temperaturemaintained at 130°
  3. customafter 1.5 hours
  4. temperatureheating
  5. filtrationfiltered through Celite
  6. customThe filtrate was evaporated to a residue
  7. customchromatographed on silica gel
  8. customevaporated

Sources & evidence

ORD record
ord-0343305172d346339c8b2788ac7ef181
Source dataset
uspto-grants-1990_01
Patent number
US04897479

Linked notes

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