Tetrahydrofuran → HCID 11782906, compound

HRID 1268715Notes

Reaction equation

HRID 1268715 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[S:16][C@H:15]([N-]C)[C@@H:14]([O:19][Si](C(C)(C)C)(C)C)[C@H:13]1[O:27][Si](C(C)(C)C)(C)C.[F-].[CH2:36]([N+:40]([CH2:49]CCC)(CCCC)CCCC)CCC.[O:53]1CCCC1>>[CH3:36][NH:40][C:49]([C@@H:15]1[C@@H:14]([OH:19])[C@@H:13]([OH:27])[C@H:12]([N:6]2[CH:5]=[N:4][C:3]3[C:7]2=[N:8][C:9]([Cl:11])=[N:10][C:2]=3[NH2:1])[S:16]1)=[O:53]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86601632HCID 86601632, compound

Product 1

HCID 11782906HCID 11782906, compoundYield 69%

Procedure

140 mg (0.24 mmol) of (2S,3S,4R,5R)-[5-(6-amino-2-chloro-purin-9-yl)-3,4-bis(tert-butyldimethylsilanyloxy)tetrahydrothiophen-2-yl]-methyl amide from the aforementioned Experimental Example 28 were dissolved in 10 mL of anhydrous tetrahydrofuran to which 0.67 mL (0.67 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=4:1) to obtain 58 mg (yield: 69%) of (2S,3S,4R,5R)-5-(6-amino-2-chloro-purin-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-5e55f10a5acf4f00a2003eab7d23bd01
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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