Anthranilic Acid → HCID 21832992, compound

HRID 1740764Notes

Reaction equation

HRID 1740764 reaction equation
C(N(CC)CC)C.[C:8]([OH:17])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].[C:18](Cl)(=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(Cl)(=O)OCC>C(Cl)Cl>[CH2:30]([C:31]1[O:16][C:8](=[O:17])[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 66986Myristoyl chloride

Product 1

HCID 21832992HCID 21832992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.76 ml) was added to a suspension of anthranilic acid (823 mg) in methylene chloride (20 ml). Then, myristoyl chloride (1.63 ml) was dropwise added to the mixture while being cooled with ice. After being stirred for 2.5 hour at room temperature, the reaction mixture was cooled with ice. Triethylamine (0.92 ml) and ethyl chlorocarbonate (0.63 ml) were dropwise added to the reaction mixture successively. After being stirred for 1 hour at 0° C. and for 1.5 hours at room temperature successively, the reaction mixture was concentrated. The residue, with ethyl acetate added thereto, was washed with water, neutralized with diluted hydrochloric acid, and washed with saturated brine. The organic layer was dried over magnesium sulfate anhydride and then concentrated. The residue was purified by silica gel column chromatography (silica gel 60 g, chloroform-hexane), thereby yielding 1.663 g of the aimed compound as colorless crystals.

Workup

  1. temperaturewhile being cooled with ice
  2. temperaturethe reaction mixture was cooled with ice
  3. stirringAfter being stirred for 1 hour at 0° C. and for 1.5 hours at room temperature successively
  4. concentrationthe reaction mixture was concentrated
  5. additionThe residue, with ethyl acetate added
  6. washwas washed with water
  7. washwashed with saturated brine
  8. dry with materialThe organic layer was dried over magnesium sulfate anhydride
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (silica gel 60 g, chloroform-hexane)

Sources & evidence

ORD record
ord-aacccd362c534720b74c8824ed59259f
Source dataset
uspto-grants-1999_10
Patent number
US05972929

Reaction notes

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