2,2-Dimethoxypropane → HCID 66618020, compound

HRID 222163Notes

Reaction equation

HRID 222163 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([N:8]2[C:12]3[N:13]=[CH:14][N:15]=[C:16]([S:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[CH:10]=[CH:9]2)[C@H:5]([OH:24])[C@@H:4]1[OH:25].CO[C:28](OC)([CH3:30])[CH3:29].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:29][C:28]1([CH3:30])[O:24][C@H:5]2[C@H:6]([N:8]3[C:12]4[N:13]=[CH:14][N:15]=[C:16]([S:17][C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:11]=4[CH:10]=[CH:9]3)[CH2:7][C@@H:3]([CH2:2][OH:1])[C@H:4]2[O:25]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 66618255HCID 66618255, compound

Product 1

HCID 66618020HCID 66618020, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(1S,2R,3S,5R)-3-(Hydroxymethyl)-5-[4-(phenylsulfanyl)-7H-pyrrolo[2,3-d]-pyrimidin-7-yl]cyclopentane-1,2-diol (320 mg, 0.0895 mmol), 2,2-dimethoxypropane (0.0549 mL, 0.446 mmol), and p-toluenesulfonic acid monohydrate (17.0 mg, 0.0895 mmol) were dissolved in acetone (2.20 mL) and stirred at rt overnight. Then the reaction was quenched with saturated sodium bicarbonate solution and approximately half the solvent was removed in vacuo. The resulting residue was diluted with water and extracted with DCM (3×). Combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a white foam (35.5 mg, 99%), which was used without further purification. LC/MS: Rt=1.72 min, ES+ 389 (FA standard).

Workup

  1. customThen the reaction was quenched with saturated sodium bicarbonate solution and approximately half the solvent
  2. customwas removed in vacuo
  3. additionThe resulting residue was diluted with water
  4. extractionextracted with DCM (3×)
  5. dry with materialCombined organics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-972168ae9d524f6bbdf0e0c896d3038c
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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