Benzyl chloroformate → N-Z-D-serine methyl ester

HRID 1620761Notes

Reaction equation

HRID 1620761 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].S(Cl)(Cl)=O.[C:12](=O)([O-])O.[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CO.O>[CH2:21]([O:20][C:18]([NH:1][C@@H:2]([C:5]([O:7][CH3:12])=[O:6])[CH2:3][OH:4])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 24386Thionyl ChlorideHCID 71077D-SerineHCID 516892Sodium Bicarbonate

Product 1

HCID 11821096N-Z-D-serine methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of D-serine (10.5 g) in methanol (100 mL) was added thionyl chloride (8.76 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 4 hr, and to the reaction mixture were added sodium hydrogen carbonate (25.2 g) and benzyl chloroformate (17.1 mL). The reaction mixture was stirred at room temperature overnight, the reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (10.3 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-867e1aa7a08b4944bf68d09f49d163f9
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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