Ethanesulfonic acid → HCID 135738512, compound

HRID 1194794Notes

Reaction equation

HRID 1194794 reaction equation
C([N:4]([C:15](=[O:17])[CH3:16])[C:5]1[NH:6][C:7](=[O:14])[C:8]2[NH:9][CH:10]=[N:11][C:12]=2[N:13]=1)(=O)C.[C:18]([O:21][CH:22]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[CH2:23][O:24][CH2:25]OC(=O)C)(=[O:20])[CH3:19].C(S(O)(=O)=O)C>>[C:15]([NH:4][C:5]1[NH:6][C:7](=[O:14])[C:8]2[N:9]=[CH:10][N:11]([CH2:25][O:24][CH2:23][CH:22]([O:21][C:18](=[O:20])[CH3:19])[CH2:30][O:31][C:32](=[O:34])[CH3:33])[C:12]=2[N:13]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 11668Ethanesulfonic acidHCID 144233211,2-Propanediol, 3-[(acetyloxy)methoxy]-, 1,2-diacetateHCID 136360183Diacetylguanine

Product 1

HCID 135738512HCID 135738512, compound

Procedure

A mixture of 2.61 g (11.1 mmole) of diacetylguanine (VII), 5.50 g (22.2 mmole) of acetoxymethyl 2,3-diacetoxy-1-propyl ether from Step A above and 55 mg of ethanesulfonic acid was heated in a flask fitted with a distillation adapter under low vacuum in an oil bath at 155°-160°. The mixture gradually thinned enough to permit magnetic stirring, and some distillate was collected. The mixture became homogenous after about 45 minutes and was cooled after 75 minutes. The viscous oil as taken up in about 100 ml of ethyl acetate and induced to crystallize with a yield of 1.23 g (29%) of nearly white crystals, mp 162.5°-165°. Thin layer chromatography (TLC) (9:1 CHCl3 --CH3OH) showed a single spot.

Workup

  1. customfitted with a distillation adapter under low vacuum in an oil bath at 155°-160°
  2. distillationsome distillate was collected
  3. temperaturewas cooled after 75 minutes
  4. customto crystallize with a yield of 1.23 g (29%) of nearly white crystals, mp 162.5°-165°

Sources & evidence

ORD record
ord-cac2c353b3044bc794b524c25c077687
Source dataset
uspto-grants-1989_03
Patent number
US04816447

Reaction notes

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