Dicyclohexylcarbodiimide → Methyl 4-(Acetylamino)-3-[(Acetoxyacetyl)Amino]Benzoate

HRID 2400189Notes

Reaction equation

HRID 2400189 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[NH2:16])(=[O:4])[CH3:3].[C:17]([O:20][CH2:21][C:22](O)=[O:23])(=[O:19])[CH3:18].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.O1CCOCC1>[C:2]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[NH:16][C:22](=[O:23])[CH2:21][O:20][C:17](=[O:19])[CH3:18])(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 83766Acetoxyacetic acidHCID 131719127Methyl 4-(Acetylamino)-3-Aminobenzoate, Hydrochloride

Product 1

HCID 10447968Methyl 4-(Acetylamino)-3-[(Acetoxyacetyl)Amino]BenzoateYield 678.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 16 (0.20 g, 0.96 mmol) was dissolved in a mixture of anhydrous DMF (2 mL) and anhydrous dioxane (5 mL), and the solution was cooled to 0°-5° C. in an ice bath. To this were added acetoxy acetic acid (0.124 g, 0.129 mmol) and DCC (0.198 g, 0.210 mL, 0.960 mmol). The reaction mixture was stirred for a few minutes at 0° C., the ice bath was removed, and the mixture was stirred at room temperature for 4 hours. The solid which separated was filtered and the filtrate was concentrated to dryness on a rotary evaporator. The solid residue was triturated with 5% HCl, filtered, and washed on the filter with water. The collected solid was then triturated with 5% NaHCO3, filtered, washed with water, and dried under vacuum to give 17 (270 mg, 70.9% yield) as a white solid: mp 182°-186° C.

Workup

  1. temperaturethe solution was cooled to 0°-5° C. in an ice bath
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred at room temperature for 4 hours
  4. customThe solid which separated
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated to dryness on a rotary evaporator
  7. customThe solid residue was triturated with 5% HCl
  8. filtrationfiltered
  9. washwashed on the
  10. filtrationfilter with water
  11. customThe collected solid was then triturated with 5% NaHCO3
  12. filtrationfiltered
  13. washwashed with water
  14. customdried under vacuum

Sources & evidence

ORD record
ord-b32e9ee7d80643fea964f7859731fe54
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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