Trichloroisocyanuric Acid → HCID 20306521, compound

HRID 1732481Notes

Reaction equation

HRID 1732481 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:24]([O:26][CH3:27])=[O:25])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:23])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:28]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)(Cl)Cl.CO>[C:1]([O:5][C:6]([NH:8][CH:9]([C:24]([O:26][CH3:27])=[O:25])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:23])[C:20]([OH:22])=[O:21])=[CH:17][C:18]=1[Cl:28])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 15283445HCID 15283445, compound

Product 1

HCID 20306521HCID 20306521, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

DL-p-(3-tert-Butoxycarbonylamino-3-methoxycarbonylpropoxy)phenylglyoxylic acid (750 mg.) was dissolved in a mixture of chloroform (15 ml.) and methanol (10 ml.), and to the solution was added 1,3,5-trichloroisocyanuric acid (180 mg.) in the course of 5 minutes, whereafter the mixture was stirred at ambient temperature for 18.7 hours. The insoluble materials were filtered off from the reaction mixture and the filtrate was evaporated to dryness under reduced pressure. The resultant residue was dissolved in ethyl acetate, and the solution was washed with water and then dried over magnesium sulfate. This solution was evaporated to dryness under reduced pressure to give a residue, which was subjected to column chromatography on silica gel (11 g.). Elution was carried out with a mixture of chloroform and methanol (99:1 by volume) and the fractions containing a desired compound were collected. The solvent was removed by evaporation from the eluate under reduced pressure to give DL-p-(3-tert-butoxycarbonylamino-3-methoxycarbonylpropoxy)-3-chlorophenylglyoxylic acid (380 mg.).

Workup

  1. filtrationThe insoluble materials were filtered off from the reaction mixture
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. dissolutionThe resultant residue was dissolved in ethyl acetate
  4. washthe solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThis solution was evaporated to dryness under reduced pressure
  7. customto give a residue, which
  8. washElution
  9. additionwas carried out with a mixture of chloroform and methanol (99:1 by volume)
  10. additionthe fractions containing a desired compound
  11. customwere collected
  12. customThe solvent was removed by evaporation from the eluate under reduced pressure

Sources & evidence

ORD record
ord-62739a2f4c7540c39be02d6dd80b28d1
Source dataset
uspto-grants-1980_12
Patent number
US04237305

Reaction notes

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