Formaldehyde → 3-{3-[(Benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl}propanoic acid

HRID 64923Notes

Reaction equation

HRID 64923 reaction equation
[C:1]1(C)C=CC=CC=1.[CH2:8]([O:15][C:16]([NH:18][C@H:19]([C:25]([OH:27])=[O:26])[CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[CH2:8]([O:15][C:16]([N:18]1[CH:19]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:25](=[O:27])[O:26][CH2:1]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1140TolueneHCID 70866L-Glutamic acid, N-((phenylmethoxy)carbonyl)-HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 5613963-{3-[(Benzyloxy)carbonyl]-5-oxo-1,3-oxazolidin-4-yl}propanoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1 liter of toluene were added 300 g of DL-N-benzyloxycarbonylglutamic acid, 48 g of paraformaldehyde and 12 g of p-toluenesulfonic acid monohydrate, and azeotropic dehydration was then carried out for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the oily substance thus obtained was dissolved in 500 ml of ethyl acetate, after which the resulting solution was washed with water and then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure to obtain oily DL-3-benzyloxycarbonyl-4-(2-carboxyethyl)oxazolidin-5-one.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by distillation under reduced pressure
  3. customthe oily substance thus obtained
  4. washafter which the resulting solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-323e31a975494d069d5ca4ba6f1a34ef
Source dataset
uspto-grants-1986_09
Patent number
US04610983

Reaction notes

Loading…