Sodium Carbonate → Dibenzyl 4-hydroxy-3,3-dimethylbutyl phosphate

HRID 2238331Notes

Reaction equation

HRID 2238331 reaction equation
[CH3:1][C:2]([CH3:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].N1C=NN=N1.C(N(CC)[P:17]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C.ClC1C=CC=C(C(OO)=[O:44])C=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.ClCCl>[P:17]([O:7][CH2:6][CH2:5][C:2]([CH3:8])([CH3:1])[CH2:3][OH:4])([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:44]

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 5066231Dibenzyl diethylphosphoramiditeHCID 108878792,2-Dimethylbutane-1,4-diolHCID 178418441HCID 178418441, compound

Product 1

HCID 67234826Dibenzyl 4-hydroxy-3,3-dimethylbutyl phosphateYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 9A (0.80 g, 6.8 mmol) and 1H-tetrazole (0.190 g) in THF (7.0 mL) at 0° C. was added dibenzyl diethylphosphoramidite (0.96 mL), and the solution was allowed to warm to room temperature and was stirred for 68 hours. To this solution was added dichloromethane (7.0 mL) and the mixture was cooled to −45° C., followed by addition of m-chloroperbenzoic acid (1.3 g). The mixture was stirred at −45° C. for 1 hour and at room temperature for 1 hour. 10% Na2CO3 was added and the reaction was extracted twice with chloroform. The combined organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient starting with 50% ethyl acetate in chloroform and ending with ethyl acetate, to give the title compound (0.922 g, 45%).

Workup

  1. temperaturethe mixture was cooled to −45° C.
  2. stirringThe mixture was stirred at −45° C. for 1 hour and at room temperature for 1 hour
  3. extractionthe reaction was extracted twice with chloroform
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel
  8. washeluting with a gradient

Sources & evidence

ORD record
ord-d55b3added924d70a9e11b6927ecfed5
Source dataset
uspto-grants-2010_05
Patent number
US07718633B2

Reaction notes

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