Sodium Chloride → HCID 20512641, compound

HRID 1164196Notes

Reaction equation

HRID 1164196 reaction equation
[CH3:1][C:2](=[CH2:34])[CH:3]([N:17]1[CH:20]([Cl:21])[CH:19]([NH:22]C(=O)COC2C=CC=CC=2)[C:18]1=[O:33])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5].P(Cl)(Cl)(Cl)(Cl)Cl.N1C2C(=CC=CC=2)C=CC=1.[Cl-].[Na+]>C(O)CC.C(Cl)(Cl)Cl>[CH3:34][C:2](=[CH2:1])[CH:3]([N:17]1[CH:20]([Cl:21])[CH:19]([NH2:22])[C:18]1=[O:33])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7047QuinolineHCID 24819Phosphorus pentachlorideHCID 13071360HCID 13071360, compound

Product 1

HCID 20512641HCID 20512641, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 5 mmoles of p-nitrobenzyl 3-methyl-2-(2-oxo-4-chloro-3-phenoxyacetamido-1-azetidinyl)-3--butenoate in 20 ml. of chloroform cooled to -10° C. were added 30 mmoles of phosphorus pentachloride and an excess of quinoline (30 mmoles plus). The reaction mixture was stirred for 30 min. and was then cooled to -30° C. To the cold mixture were added 2 ml. of n-propyl alcohol with stirring and the reaction mixture was allowed to stand in an ice bath for about 3 min. Thereafter 5 ml. of a saturated aqueous solution of sodium chloride were added followed by the addition of 100 ml. of petroleum ether. The product precipitated as a gum from which the liquid phase was decanted. The gum solidified on treatment with 5 ml. of saturated aqueous sodium chloride. The product was filtered and dried. There were obtained 400 mg. of the deacylated product as the hydrochloride salt represented by the following formula. ##STR56## wherein pNB=p-nitrobenzyl.

Workup

  1. additionTo the cold mixture were added 2 ml
  2. waitto stand in an ice bath for about 3 min
  3. additionfollowed by the addition of 100 ml
  4. customThe product precipitated as a gum from which the liquid phase
  5. customwas decanted
  6. filtrationThe product was filtered
  7. customdried
  8. customThere were obtained 400 mg

Sources & evidence

ORD record
ord-49085013982b46db9aa61a1e1cfd3766
Source dataset
uspto-grants-1983_01
Patent number
US04368156

Reaction notes

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