Water → HCID 14390432, compound

HRID 1709579Notes

Reaction equation

HRID 1709579 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:25](OCC)(=[O:27])C>C(O)CO>[ClH:20].[OH:27][CH2:25][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

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 14390525HCID 14390525, compound

Product 1

HCID 14390432HCID 14390432, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of (R)-N-[3-[(4-chlorobenzoyl)amino]-2-pyridinyl]alanine methyl ester (42.5 g, 0.0127 mole) in ethylene glycol (250 ml) was refluxed under nitrogen for one hour. The solution was cooled to room temperature and approximately 5 ml of the solution was added to water. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted with two additional portions of ethyl acetate and the combined organic layers were washed three times with a saturated sodium chloride solution. The ethyl acetate layer was dried over sodium sulfate, filtered, and evaporated to an oil under reduced pressure. The oil was dissolved in isopropyl alcohol and was made acidic with hydrogen chloride/isopropyl alcohol. Addition of isopropyl ether to the cloud point gave a solid. The solid was collected by filtration, rinsed with isopropyl ether and dried under high vacuum at room temperature to give 0.25 g of title compound, mp 191°-195° C.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with two additional portions of ethyl acetate
  3. washthe combined organic layers were washed three times with a saturated sodium chloride solution
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil under reduced pressure
  7. dissolutionThe oil was dissolved in isopropyl alcohol
  8. additionAddition of isopropyl ether to the cloud point
  9. customgave a solid
  10. filtrationThe solid was collected by filtration
  11. washrinsed with isopropyl ether
  12. customdried under high vacuum at room temperature

Sources & evidence

ORD record
ord-e7f3f59851fd4d668e5a137ea62656db
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

Loading…