Sulfuric Acid → 5-(Methyl-propylcarbamoyl)-isophthalic acid 1-ethyl ester 3-isopropyl ester

HRID 1436623Notes

Reaction equation

HRID 1436623 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:13]=[C:12]([C:14](=[O:20])[N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1)[CH3:2].S(=O)(=O)(O)O.ON1[C:32]2C=CC=C[C:31]=2N=N1.Cl.[CH3:38]N(C)CCCN=C=NCC>C(N(CC)CC)C.C(O)(C)C>[CH:1]([O:3][C:4](=[O:21])[C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:14](=[O:20])[N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:13]=1)[C:8]([O:10][CH2:31][CH3:32])=[O:9])([CH3:38])[CH3:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 688146805-(Methyl-propylcarbamoyl)-isophthalic acid monoethyl ester

Product 1

HCID 688145695-(Methyl-propylcarbamoyl)-isophthalic acid 1-ethyl ester 3-isopropyl ester

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

Sonicate a mixture of 5-(methyl-propyl-carbamoyl)-isophthalic acid monoethyl ester (146 mg, 0.5 mmol), isopropanol (0.75 mL) and concentrated sulfuric acid (25 μL) then stir the resulting solution at room temperature for one month. Add 1-hydroxybenzotriazole (68 mg, 0.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (96 mg, 0.5 mmol), and triethylamine (100 μL). Stir overnight at room temperature. Add dichloromethane (25 mL) and wash with 0.1 N citric acid (5 mL), saturated aqueous sodium bicarbonate (10 mL), saturated aqueous sodium chloride (10 mL), dry (magnesium sulfate) and concentrate (149 mg, 89%).

Workup

  1. customSonicate
  2. stirringStir overnight at room temperature
  3. washAdd dichloromethane (25 mL) and wash with 0.1 N citric acid (5 mL), saturated aqueous sodium bicarbonate (10 mL), saturated aqueous sodium chloride (10 mL)
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate (149 mg, 89%)

Sources & evidence

ORD record
ord-cae70307719143448798e96bf0d52da0
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…