Phosgene → HCID 18923957, compound

HRID 1600100Notes

Reaction equation

HRID 1600100 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].[C:13](Cl)(Cl)=[O:14]>C1(C)C=CC=CC=1>[O:14]=[C:13]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

4

Reactant 2

HCID 6371PhosgeneHCID 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 tetrahydrofuranand 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-7f924c0954164e0fb4650e519da303b2
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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