Sodium hydride → HCID 86589696, compound

HRID 2299639Notes

Reaction equation

HRID 2299639 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][N:15]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(O[CH2:32][C@H:33]1[O:35][CH2:34]1)(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:3]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:32][C@@H:33]2[CH2:34][O:35]2)=[CH:16][N:15]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 516892Sodium BicarbonateHCID 18007173HCID 18007173, compound

Product 1

HCID 86589696HCID 86589696, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under nitrogen, to a suspension of sodium hydride (60% in oil, 189 mg) in N,N-dimethylformamide (20 ml) was dropwise added 2-benzyloxycarbonylamino-5-hydroxypyridine (1.1 g) in N,N-dimethylformamide (12 ml) at 5° C., and the mixture was stirred at room temperature for 1 hour. To this one was added (2S)-(+)-1-tosyloxy-2,3-epoxypropane (1.1 g) at 5° C., and the mixture was stirred at room temperature for 7 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=9:1) to give 2-benzyloxycarbonylamino-5-[(2S)-oxiranylmethoxy]pyridine (780 mg).

Workup

  1. customat 5° C.
  2. stirringthe mixture was stirred at room temperature for 7 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-eb781d296f9c4ccda37a51c70260110f
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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