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

HRID 1450335Notes

Reaction equation

HRID 1450335 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-2bbc630488cc4a7d9cd664da9e9b0778
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Reaction notes

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