Potassium Carbonate → HCID 58296236, compound

HRID 552773Notes

Reaction equation

HRID 552773 reaction equation
C([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]=3[C:12]([C:27]#[C:28][Si](C)(C)C)=[CH:11]2)[O:7][C@@H:6]1[CH2:33][O:34][S:35]([NH2:38])(=[O:37])=[O:36])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[S:35](=[O:36])(=[O:37])([O:34][CH2:33][C@@H:6]1[C@@H:5]([OH:4])[CH2:9][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]=3[C:12]([C:27]#[CH:28])=[CH:11]2)[O:7]1)[NH2:38]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86607338HCID 86607338, compound

Product 1

HCID 58296236HCID 58296236, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,3S,5R)-2-{[(aminosulfonyl)oxy]methyl}-5-{4-(2-phenylethyl)-5-[(trimethylsilyl)ethynyl]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}tetrahydrofuran-3-yl acetate (0.254 g, 0.457 mmol) in MeOH (5 mL) at r.t. was added K2CO3 (0.168 g, 1.22 mmol) and the mixture was stirred for 2 h. The reaction mixture was diluted with CH2Cl2, washed with saturated aq NaHCO3 dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (0 to 10% MeOH/DCM) to give the title compound (0.126 g, 62%).

Workup

  1. washwashed with saturated aq NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-da2ebd5df8ed43eba2b1a3ada68cdbbb
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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