Thionyl Chloride → Methyl (4S)-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate

HRID 968312Notes

Reaction equation

HRID 968312 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:14][OH:15])[NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O>C(Cl)Cl>[C:7]1([C:6]2[O:15][CH2:14][C@@H:4]([C:3]([O:2][CH3:1])=[O:16])[N:5]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 2222571HCID 2222571, compound

Product 1

HCID 11074512Methyl (4S)-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylateYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of N-benzoyl-L-serine methyl ester (21.0 g), thionyl chloride (21.0 g), and methylene chloride (150 ml) is stirred at reflux for 1 hour. The solvent is evaporated and the residue is diluted with cold water. Neutralize with sodium bicarbonate, and extract with ethyl acetate. Purification on silica gel (250 g), eluting with methanol:methylene chloride (01:99), yields methyl (S)-2-phenyl-2-oxazoline-4-carboxylate (15.2 g).

Workup

  1. temperatureat reflux for 1 hour
  2. customThe solvent is evaporated
  3. additionthe residue is diluted with cold water
  4. extractionNeutralize with sodium bicarbonate, and extract with ethyl acetate
  5. customPurification on silica gel (250 g)
  6. washeluting with methanol:methylene chloride (01:99)

Sources & evidence

ORD record
ord-a8736c94d02b4bf987b23674f1adbe4c
Source dataset
uspto-grants-2005_10
Patent number
US06958355B2

Reaction notes

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