Pentachlorophenol → Perchlorophenyl 5-oxo-L-prolinate

HRID 972701Notes

Reaction equation

HRID 972701 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[Cl:10][C:11]1[C:16](O)=[C:15]([Cl:18])[C:14]([Cl:19])=[C:13]([Cl:20])[C:12]=1[Cl:21].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:10][C:11]1[C:16]([O:8][C:7](=[O:9])[C@@H:2]2[CH2:3][CH2:4][C:5](=[O:6])[NH:1]2)=[C:15]([Cl:18])[C:14]([Cl:19])=[C:13]([Cl:20])[C:12]=1[Cl:21]

Participants

5

Reactant 3

HCID 992PentachlorophenolHCID 7405L-Pyroglutamic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 3035255Perchlorophenyl 5-oxo-L-prolinateYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

129 g (1mol) of L-pyroglutamic acid were finely ground in a mortar and suspended in 2 l of tetrahydrofurane. 319 g (1.2 mol) of pentachlorophenol and, at 0° C., 220 g (1.06 mol) of dicyclohexylcarbodiimide dissolved in 300 ml of tetrahydrofurane were added. The mixture was stirred for 1 hour at 0° C. and for 5 hours at room temperature. The dicyclohexyl urea was filtered off, and extracted with a small amount of warm tetrahydrofurane. The solvent was distilled off in vacuum. The residue was boiled with isopropanol and filtered off after cooling. After drying under vacuum over P2O5 and KOH, 175 g product were obtained which melted at 198° C., [α]D20 = + 18.6° (c=1, dimethyl formamide)

Workup

  1. additionwere added
  2. filtrationThe dicyclohexyl urea was filtered off
  3. extractionextracted with a small amount of warm tetrahydrofurane
  4. distillationThe solvent was distilled off in vacuum
  5. filtrationfiltered off
  6. temperatureafter cooling
  7. dry with materialAfter drying under vacuum over P2O5 and KOH

Sources & evidence

ORD record
ord-a9cee7bf1777431eb0064079e43c2421
Source dataset
uspto-grants-1977_10
Patent number
US04053588

Reaction notes

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