Sodium Bicarbonate → (S)-oxiranylmethyl-carbamic acid benzyl ester

HRID 2228862Notes

Reaction equation

HRID 2228862 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][CH2:11][C@H:12]([OH:15])[CH2:13]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].C[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:16])[NH:10][CH2:11][C@@H:12]1[O:15][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 10942334Sodium MethoxideHCID 11310670benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate

Product 1

HCID 10375722(S)-oxiranylmethyl-carbamic acid benzyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(S)-2,3-Dihydroxy-1-propylcarbamate benzyl ester (2.11 g, 0.01 mol) in 100 ml flask was dissolved in CHCl3 (30 ml). 1-Chlorocarbonyl-1-methylethylacetate (1.8 ml, 0.013 mol) was added and stirred for 3 hours at ambient temperature. Sat. aqueous solution of NaHCO3 (20 ml) was added and extracted three times with ethyl acetate (50 ml). The organic layer was evaporated and dissolved in THF (50 ml). Sodium methoxide (0.53 g, 0.01 mol) was added and stirred for 6 hours. Sat. aqueous solution of NaHCO3 (50 ml) was added and extracted with ethyl acetate (50 ml). The organic layer was dried over anhydrous MgSO4 and evaporated to dryness. The crude product was purified by column chromatography on silica gel to give (S)-2,3-epoxy-1-propylcarbamate benzyl ester (90%, optical purity>99%ee).

Workup

  1. extractionextracted three times with ethyl acetate (50 ml)
  2. customThe organic layer was evaporated
  3. dissolutiondissolved in THF (50 ml)
  4. stirringstirred for 6 hours
  5. extractionextracted with ethyl acetate (50 ml)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. customevaporated to dryness
  8. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7fce327d3be8414bab7091212ab0b61d
Source dataset
uspto-grants-2002_07
Patent number
US06417403B1

Reaction notes

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