Water → HCID 86598073, compound

HRID 895866Notes

Reaction equation

HRID 895866 reaction equation
C1([CH:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])[OH:5])CC1.[H-].[Na+].[N+]([C:19]1[CH:20]=[C:21](S(OC[C@@H]2OC2)(=O)=O)[CH:22]=[CH:23][CH:24]=1)([O-])=O.[OH2:33]>CN(C)C=O>[CH:22]1([CH:21]([O:5][CH2:4][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])[C@H:20]2[CH2:19][O:33]2)[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 22382435HCID 22382435, compound

Product 1

HCID 86598073HCID 86598073, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Cyclopropyl)(2-methoxyphenyl)methanol (3.57 g) obtained in Step 1 was dissolved in N,N-dimethylformamide (50 ml), sodium hydride (960 mg, 60% oil) was added and the mixture was stirred for 3 min. To the resulting mixture was added (R)-glycidyl 3-nitrobenzenesulfonate (6.22 g) and the mixture was stirred at room temperature for 12 hr. The reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=88:12) to give the title compound (1.10 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=88:12)

Sources & evidence

ORD record
ord-9b7feb1e40924e5cb1753c55990f3611
Source dataset
uspto-grants-2005_07
Patent number
US06916956B2

Reaction notes

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