Dicyclohexylcarbodiimide → Methyl 4-(Acetylamino)-3-[(2,3-Diacetoxypropanoyl)Amino]Benzoate

HRID 2400190Notes

Reaction equation

HRID 2400190 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][CH:21]([CH2:25][O:26][C:27](=[O:29])[CH3:28])[C:22](O)=[O:23])(=[O:19])[CH3:18].C1(N=C=NC2CCCCC2)CCCCC1>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])[CH:21]([O:20][C:17](=[O:19])[CH3:18])[CH2:25][O:26][C:27](=[O:29])[CH3:28])(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 147372062,3-Diacetoxypropanoic acidHCID 131719127Methyl 4-(Acetylamino)-3-Aminobenzoate, Hydrochloride

Product 1

HCID 10022657Methyl 4-(Acetylamino)-3-[(2,3-Diacetoxypropanoyl)Amino]BenzoateYield 92.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 16 (0.12 g, 0.57 mmol) was dissolved in a mixture of DMF (2 mL) and dioxane (3 mL) and cooled to 0° C. A solution of 2,3-diacetoxypropionic acid (0.220 g, 1.15 mmol) in dioxane (3 mL) was added followed by the addition of dicyclohexylcarbodiimide (0.195 mL, 0.183 g, 0,870 mmol). The resulting reaction mixture was stirred for 3 hours, initially at 0° C. with slow warming to room temperature. The solid dicyclohexylurea which separated was filtered and the filtrate was concentrated to dryness on a rotary evaporator. The solid residue was filtered and washed on the filter with 5% HCl (5 mL), water (5 mL), 5% NaHCO3 (5 mL), and again with water (2×10 mL). This was dried under vacuum to give 18 (200 mg, 91.3%) as a white solid: mp 130°-134° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewith slow warming to room temperature
  3. customThe solid dicyclohexylurea which separated
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated to dryness on a rotary evaporator
  6. filtrationThe solid residue was filtered
  7. washwashed on the
  8. filtrationfilter with 5% HCl (5 mL), water (5 mL), 5% NaHCO3 (5 mL)
  9. customThis was dried under vacuum

Sources & evidence

ORD record
ord-dc8bd11753ea44079bf688fa05f483d1
Source dataset
uspto-grants-1995_09
Patent number
US05453533

Reaction notes

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