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

HRID 64934Notes

Reaction equation

HRID 64934 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 300 ml of toluene were added 100 g of DL-N-benzyloxycarbonylglutamic acid, 20 g of powdery paraformaldehyde and 4 g of p-toluenesulfonic acid monohydrate, and the resulting mixture was subjected to azeotropic dehydration for 3 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and the oily product thus obtained was dissolved in 200 ml of ethyl acetate, after which the resulting solution was washed with water. The organic layer thus formed was then separated and 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. Thus product was dissolved in 250 ml of toluene with heating, and 120 g of n-propylamine was added thereto, after which the resulting mixture was heated under reflux for 3.5 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in 250 ml of ethyl acetate, after which the resulting solution was washed with three 100-ml portions of diluted hydrochloric acid. The resulting organic layer was separated, and the pH thereof was adjusted to 10 with a 3% aqueous sodium hydroxide solution, after which the resulting aqueous layer was separated. The pH of the aqueous layer was adjusted to 6 with diluted hydrochloric acid, and the crystals thus precipitated were collected by filtration to obtain 87 g (yield 76%) of DL-N2 -benzyloxycarbonyl-N1 -n-propyl-α-glutamylamide having a melting point of 132°-135° C.

Workup

  1. customSubsequently, the solvent was removed by distillation under reduced pressure
  2. customthe oily product thus obtained
  3. washafter which the resulting solution was washed with water
  4. customThe organic layer thus formed
  5. customwas then separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-e14f326f6eb34eb0bb754d0bc8152a46
Source dataset
uspto-grants-1986_09
Patent number
US04610983

Reaction notes

Loading…