3,4-Dichlorobenzoic acid → HCID 19754789, compound

HRID 1588856Notes

Reaction equation

HRID 1588856 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=O.[NH2:12][CH2:13][C:14]([N:16]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15]>CN(C)C1C=CN=CC=1.ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:12][CH2:13][C:14]([N:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:23][C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:15])=[O:7]

Participants

5

Reactant 2

HCID 58173,4-Dichlorobenzoic acidHCID 18951114HCID 18951114, compound

Product 1

HCID 19754789HCID 19754789, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

4-Dimethylaminopyridine (5 mg) and then N,N'-carbonyldiimidazole (1.78 g) are added to a solution of 3,4-dichlorobenzoic acid (1.91 g) in anhydrous 1,2-dichloroethane (50 cc). The solution obtained is stirred for 2 hours at a temperature in the region of 20° C., tert-butyl 2-(2-amino-N-phenylacetamido)acetate (2.64 g) is then added and the mixture is stirred for 3 hours at a temperature in the region of 20° C. The reaction mixture is then washed with water (3×75 cc), and the organic phase is separated, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is purified by chromatography on silica gel (0.04-0.063 mm; 250 g) contained in column 4.2 cm in diameter [eluant: dichloromethane/methanol (98:2 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 20-cc fractions. Fractions 7 to 15 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. and the residue is recrystallized in a mixture of cyclohexane and 2-propanol (80:20 by volume). tert-Butyl N-[N- (3,4-dichlorobenzoyl)glycyl]-N-phenylglycinate (1.5 g), m.p. 95° C., is thereby obtained.

Workup

  1. customThe solution obtained
  2. additionis then added
  3. washThe reaction mixture is then washed with water (3×75 cc)
  4. customthe organic phase is separated
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel (0.04-0.063 mm; 250 g)
  9. customcollecting 20-cc fractions
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C.
  11. customthe residue is recrystallized in a mixture of cyclohexane and 2-propanol (80:20 by volume)

Sources & evidence

ORD record
ord-d20d1992ea9b40178fae36df9a613be5
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

Loading…