2,2-Dimethoxypropane → HCID 66798200, compound

HRID 447647Notes

Reaction equation

HRID 447647 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][C@@H:6]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]3[C:25]4[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=4[CH:19]=[CH:18][CH:17]=3)[N:12]=[CH:11][N:10]=2)[C@H:5]([OH:26])[C@@H:4]1[OH:27].CO[C:30](OC)([CH3:32])[CH3:31].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[CH3:31][C:30]1([CH3:32])[O:26][C@H:5]2[C@H:6]([NH:8][C:9]3[CH:14]=[C:13]([NH:15][C:16]4[C:25]5[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=5[CH:19]=[CH:18][CH:17]=4)[N:12]=[CH:11][N:10]=3)[CH2:7][C@H:3]([CH2:2][OH:1])[C@H:4]2[O:27]1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66797990HCID 66797990, compound

Product 1

HCID 66798200HCID 66798200, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of (1S,2R,3R,5R)-3-(hydroxymethyl)-5-{[6-(5,6,7,8-tetrahydronaphthalen-1-ylamino)pyrimidin-4-yl]amino}cyclopentane-1,2-diol (70.0 mg, 0.19 mmol) in acetone (5.00 mL) was added 2,2-dimethoxypropane (0.21 mL, 1.70 mmol) and pyridinium p-toluenesulfonate (57.0 mg, 0.23 mmol), and the mixture was stirred for 55 h. The reaction mixture was quenched by addition of saturated NaHCO3 solution (50.0 mL) and then extracted with ethyl acetate (3×50.0 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by flash chromatography (2 to 10% Methanol/DCM) to afford the title compound (72.0 mg, 85%) as a light yellow amorphous solid. LC/MS: Rt=1.59 min, ES+ 411.3 (AA standard).

Workup

  1. customThe reaction mixture was quenched by addition of saturated NaHCO3 solution (50.0 mL)
  2. extractionextracted with ethyl acetate (3×50.0 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customThe residue was purified by flash chromatography (2 to 10% Methanol/DCM)

Sources & evidence

ORD record
ord-ff313338af3f47cf9978d6bb3c586c7e
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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