Methanol → HCID 67164148, compound

HRID 552713Notes

Reaction equation

HRID 552713 reaction equation
[C@@H:1]1([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@H:20]2[C@:24]([CH3:26])([OH:25])[C@H:23]([OH:27])[C@@H:22]([CH2:28][OH:29])[O:21]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.O.[C:31]1(C)[CH:36]=CC(S(O)(=O)=O)=C[CH:32]=1.COC(OC)(C)C.CO>CC(C)=O.C(Cl)(Cl)Cl>[C@@H:1]1([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@H:20]2[C@:24]3([CH3:26])[O:25][C:31]([CH3:36])([CH3:32])[O:27][C@@H:23]3[C@@H:22]([CH2:28][OH:29])[O:21]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 887MethanolHCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 67164927HCID 67164927, compound

Product 1

HCID 67164148HCID 67164148, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

A solution of (2R,3R,4R,5R)-2-(6-((S)-2,3-dihydro-1H-inden-1-ylamino)-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol (0.21 g, 0.53 mmol), p-toluenesulfonic acid monohydrate (0.10 g, 0.53 mmol), 2,2-dimethoxypropane (1.0 mL, 8.1 mmol) in acetone (5 mL) was stirred for 8 h. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (25 mL) and saturated sodium bicarbonate (15 mL), the aqueous was extracted with ethyl acetate and the organic phases combined, dried (MgSO4) and concentrated in vacuo. Flash chromatography (2% methanol in chloroform) gave the title compound 0.155 g, 67% yield.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate (25 mL) and saturated sodium bicarbonate (15 mL)
  3. extractionthe aqueous was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-75e0375238474e9cb6cf98fbd393b5cc
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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