Phosgene → HCID 18923957, compound

HRID 54776Notes

Reaction equation

HRID 54776 reaction equation
[CH2:1]([CH2:7][CH:8]([NH2:12])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[O:13]1CCC[CH2:14]1.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[O:13]=[C:14]1[NH:12][CH:8]([CH2:7][CH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[C:9](=[O:11])[O:10]1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 1011222-Aminopimelic acid

Product 1

HCID 18923957HCID 18923957, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

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.

Workup

  1. customArgon is bubbled through the reaction
  2. customto remove the excess phosgene
  3. customthe solvents are removed under house vacuum
  4. dissolutionThe resulting oil is dissolved in 14 ml of ethyl alcohol
  5. additiondiluted with 14 ml of petroleum ether
  6. customThe formed crystals are collected
  7. customdried

Sources & evidence

ORD record
ord-d0a0fd2d1d4e4ea6aa4e79b55d1e6f4c
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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