Trityl chloride → [(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl tritylsulfamate

HRID 552762Notes

Reaction equation

HRID 552762 reaction equation
[S:1](=[O:26])(=[O:25])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[C@H:7]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[Cl:24])[O:6]1)[NH2:2].CCN(C(C)C)C(C)C.[C:36](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[C:36]([NH:2][S:1](=[O:26])(=[O:25])[O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10]([CH3:13])([CH3:14])[O:11]2)[C@H:7]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[Cl:24])[O:6]1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 86607326((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

Product 1

HCID 86607333[(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl tritylsulfamateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate (13.4 g, 33.1 mmol) in DCM (330 mL) at r.t. was added DIPEA (11.5 mL, 66.2 mmol) followed by Ph3CCl (9.23 g, 33.1 mmol). The reaction was stirred at r.t. for 4 hours. The mixture was diluted with DCM, the layers were separated, and the organic layer was washed with 1N HCl followed by brine. The combined organic phases were dried (Na2SO4) and concentrated to yield the title compound as a white solid (17.6 g, 82%).

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with 1N HCl
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ab7c065fc6924f9eaafa439c9887b694
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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