Ethylene Glycol → HCID 14390430, compound

HRID 622037Notes

Reaction equation

HRID 622037 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([CH3:22])[NH:5][C:6]1[C:11]([NH:12][C:13](=O)[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=[CH:8][N:7]=1.O.C(O)[CH2:26][OH:27]>>[OH:27][CH2:26][CH2:1][O:2][C:3](=[O:23])[C@@H:4]([CH3:22])[N:5]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:11]2[N:12]=[C:13]1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 14390525HCID 14390525, compound

Product 1

HCID 14390430HCID 14390430, compoundYield 96%

Procedure

A solution of (R)-N-[3-[(4-chlorobenzoyl)amino]-2-pyridinyl]alanine methyl ester (27.4 g, 0.0822 mole) in ethylene glycol (150 ml) was refluxed under nitrogen for 1.75 hours and then cooled. One-third of this solution was added to water (1 liter), extracted with ethyl acetate twice and the combined organic layers were washed three times with water and once with a saturated sodium chloride solution. The organic layers was dried over magnesium sulfate, treated with charcoal, filtered, and evaporated to give 8.3 g of a yellow solid (96% yield). The solid was dissolved in hot isopropyl ether (with a little isopropyl alcohol) and filtered hot. Upon cooling to room temperature, solid precipitated, which was collected by filtration, rinsed with isopropyl ether, and dried under high vacuum at room temperature to give 3.29 g of title compound, mp 110°-113° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate twice
  3. washthe combined organic layers were washed three times with water
  4. dry with materialThe organic layers was dried over magnesium sulfate
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4cf26c2c556e45da86647d52da8a9013
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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