Reaction #83054

Reaction equation

DL-2-aminopimelic acid

tetrahydrofuran

phosgene

→

desired product

2,5-Dioxo-4-oxazolidinepentanoic acid

Solvents

toluene

Conditions

Workup

1. 1
   OtherArgon is bubbled through the reaction
2. 2
   Otherto remove the excess phosgene
3. 3
   Otherthe solvents are removed under house vacuum
4. 4
   workup.DISSOLUTIONThe resulting oil is dissolved in 14 ml of ethyl alcohol
5. 5
   workup.ADDITIONdiluted with 14 ml of petroleum ether
6. 6
   OtherThe formed crystals are collected
7. 7
   Otherdried

Procedure

A suspension of 1.752 g of DL-2-aminopimelic acid, 55 ml of tetrahydrofuran and 16 ml of 1.93M phosgene in toluene is heated, in an oil bath, at 50° C. for 1 hour. Argon is bubbled through the reaction to remove the excess phosgene and the solvents are removed under house vacuum. The resulting oil is dissolved in 14 ml of ethyl alcohol, diluted with 14 ml of petroleum ether and the solution stored overnight at room temperature. The formed crystals are collected and dried to give 1.6 g of the desired product.

Source