L-Phenylalanine → (4S)-4-Benzyl-1,3-oxazolidine-2,5-dione

HRID 54806Notes

Reaction equation

HRID 54806 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:14]([O:17]C(Cl)=O)(Cl)Cl>O1CCCC1>[C:4]1([CH2:3][C@H:2]2[C:10](=[O:12])[O:11][C:14](=[O:17])[NH:1]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6140L-Phenylalanine2×HCID 10426Diphosgene

Product 1

HCID 13517184(4S)-4-Benzyl-1,3-oxazolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.9 g of L-phenylalanine, 4.8 ml of trichloromethylchloroformate (Diphosgene), 70 ml of dry tetrahydrofuran and 0.135 g of activated carbon is heated in an oil bath at 55° C. for 2 hours, until the L-phenylalanine is in solution. The reaction is filtered through diatomaceous earth. The filtrate is concentrated in vacuo, treated with diethyl ether and hexane, and the resulting crystals are collected to give 1.04 g of the desired product.

Workup

  1. filtrationThe reaction is filtered through diatomaceous earth
  2. concentrationThe filtrate is concentrated in vacuo
  3. additiontreated with diethyl ether and hexane
  4. customthe resulting crystals are collected

Sources & evidence

ORD record
ord-09040c0caae64fb99cc55b49ecaf4a38
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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