Water → N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

HRID 653386

Reaction equation

HRID 653386 reaction equation
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH2:18](N(CC)CC)C.COS(OC)(=O)=O.O>CN(C)C=O>[CH3:18][O:16][C:15](=[O:17])[C@H:12]([CH2:13][OH:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 8471TriethylamineHCID 100310N-(Benzyloxycarbonyl)-L-serine

Product 1

HCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-CBZ-L-serine (25 g) was dissolved in 100 ml of dry N,N-dimethylformamide at 0° C. under argon. Triethylamine (2 e.g., 30 ml) and dimethylsulfate (20 ml) were added. The contents of the vessel were stirred overnight at room temperature and then poured into 500 ml of water and extracted with ethyl acetate (3×200 ml). The organic layer was washed with water and brine and dried with sodium sulfate. Rotary evaporation afforded an oil which crystallized after silica gel chromatography in pure ethyl ether. The structure of the product, N-CBZ-L-serine methyl ester, was confirmed by NMR spectroscopy.

Workup

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. customRotary evaporation
  5. customafforded an oil which
  6. customcrystallized after silica gel chromatography in pure ethyl ether

Sources & evidence

ORD record
ord-49d76b88f95e44b78687b03e026d330d
Source dataset
uspto-grants-1987_06
Patent number
US04676989

Linked notes

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