HCID 18660664, compound → HCID 18660673, compound

HRID 1266903Notes

Reaction equation

HRID 1266903 reaction equation
[Si]([O:8][C@@H:9]1[C@:13]([C:15]#[C:16][Si:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([OH:14])[C@@H:12]([CH2:36][OH:37])[O:11][C@H:10]1[N:38]1[CH:45]=[CH:44][C:42](=[O:43])[NH:41][C:39]1=[O:40])(C(C)(C)C)(C)C.Cl.CO>>[C:18]1([Si:17]([C:16]#[C:15][C@@:13]2([OH:14])[C@@H:12]([CH2:36][OH:37])[O:11][C@@H:10]([N:38]3[CH:45]=[CH:44][C:42](=[O:43])[NH:41][C:39]3=[O:40])[C@@H:9]2[OH:8])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 18660664HCID 18660664, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 18660673HCID 18660673, compoundYield 88%

Procedure

Added to 1.3 g of 1-(2-O-(tert-butyldimethylsilyl)-3-C-triphenylsilylethynyl-β-D-ribofuranosyl)uracil obtain above were 30 ml of a 2.6% (w/v) hydrochloric acid/methanol solution, and the mixture was stirred at room temperature. After 110 minutes, the solvent was distilled off under reduced pressure, and the residue was then azeotropically distilled with ethanol, purified by column chromatography on covered silica gel (chloroform:methanol=20:1-15:1) and then suspended in hexane. The suspension was filtered to obtain 940 mg (yield: 86%) of the title compound as a pale-yellow powdered substance.

Workup

  1. customobtain
  2. distillationthe solvent was distilled off under reduced pressure
  3. distillationthe residue was then azeotropically distilled with ethanol
  4. custompurified by column chromatography on covered silica gel (chloroform:methanol=20:1-15:1)
  5. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-b9ac2a2bc6bb40788a8f6aba3c6ca848
Source dataset
uspto-grants-2003_04
Patent number
USRE038090E1

Reaction notes

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