2,2-Dimethoxypropane → HCID 66798200, compound

HRID 1747641Notes

Reaction equation

HRID 1747641 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-1c213944280c440b9660417d37fad070
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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