Tetrahydrofuran → HCID 73239169, compound

HRID 1268716Notes

Reaction equation

HRID 1268716 reaction equation
CNC([C@@H:5]1[C@@H:9]([O:10][Si](C(C)(C)C)(C)C)[C@@H:8]([O:18][Si](C(C)(C)C)(C)C)[C@H:7]([N:26]2[CH:34]=[N:33][C:32]3[C:27]2=[N:28][C:29]([Cl:37])=[N:30][C:31]=3[NH:35][CH3:36])[S:6]1)=O.[F-].[CH2:39]([N+:43]([CH2:52]CCC)(CCCC)CCCC)CCC.[O:56]1CCCC1>>[CH3:39][NH:43][C:52]([C:7]1([N:26]2[CH:34]=[N:33][C:32]3[C:27]2=[N:28][C:29]([Cl:37])=[N:30][C:31]=3[NH:35][CH3:36])[CH:8]([OH:18])[CH:9]([OH:10])[CH2:5][S:6]1)=[O:56]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86601634HCID 86601634, compound

Product 1

HCID 73239169HCID 73239169, compoundYield 65%

Procedure

48 mg (0.08 mmol) of (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2-chloro-6-methylaminopurin-9-yl)-tetrahydrothiophene-2-carboxylic acid methyl amide were dissolved in anhydrous tetrahydrofuran to which 0.22 mL (0.22 mmol, 1M tetrahydrofuran solution) of tetrabutylammonium fluoride was added. The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was distilled under reduced pressure and the concentrate was purified by silica gel column chromatography using the eluant (dichloromethane:methanol=6:1) to obtain 19 mg (yield: 65%) of (2S,3S,4R,5R)-5-(2-chloro-6-methylaminopurin-9-yl-3,4-dihydroxytetrahydrothiophene-2-carboxylic acid methyl amide as white solids (see Table 3).

Workup

  1. additionwas added
  2. distillationThe reaction mixture was distilled under reduced pressure
  3. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f577aff97383467c88e91fd732a5ed48
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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