Methanol → HCID 12044465, compound

HRID 1860163Notes

Reaction equation

HRID 1860163 reaction equation
[CH:1]1([CH2:6][CH:7]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[C:8]([NH:10][C:11](=[O:18])[NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27]O>S(=O)(=O)(O)O.O>[CH3:27][O:16][C:15](=[O:17])[CH2:14][CH2:13][NH:12][C:11]([NH:10][C:8](=[O:9])[CH:7]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:18]

Participants

5

Reactant 2

HCID 887MethanolHCID 18626620HCID 18626620, compound

Product 1

HCID 12044465HCID 12044465, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-{3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-propionic acid (20 mg, 0.05 mmol) in methanol (5 mL) was treated with concentrated sulfuric acid (4 drops). This solution was heated to 80° C. for 8 h. At this time, the reaction was cooled to 25° C. and diluted with water (10 mL). This solution extracted with ethyl acetate (3×20 mL). The organics were washed with a saturated aqueous sodium bicarbonate solution (1×20 mL), a saturated aqueous sodium chloride solution (1×20 mL) and water (1×10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded 3-{3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-ureido}-propionic acid methyl ester (18 mg, 86%) as a white solid: 93.6-95.8° C.: EI-HRMS m/e calcd for C19H24Cl2N2O4 (M+) 414.1113, found 414.1114.

Workup

  1. temperatureAt this time, the reaction was cooled to 25° C.
  2. extractionThis solution extracted with ethyl acetate (3×20 mL)
  3. washThe organics were washed with a saturated aqueous sodium bicarbonate solution (1×20 mL)
  4. dry with materiala saturated aqueous sodium chloride solution (1×20 mL) and water (1×10 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa5ff3b682bf4171ab04cc38d10ea4bd
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

Loading…