Water → HCID 14390428, compound

HRID 623114Notes

Reaction equation

HRID 623114 reaction equation
C[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.[OH-].[K+]>C(O)CO>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:5]([C@H:4]([CH3:22])[C:3]([OH:2])=[O:23])[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:11]3[N:12]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 14390525HCID 14390525, compound

Product 1

HCID 14390428HCID 14390428, compoundYield 4.7%

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, 0.127 mole) in ethylene glycol 8250 ml) was refluxed under nitrogen atmosphere for one hour and then cooled. Water (40 ml) and solid potassium hydroxide pellets (10.13 g, 0.181 mole) were added and the solution was refluxed for an additional two hours, filtered into ice water (1 liter) and acidifed with 3N hydrochloric acid solution to give a solid which was collected by filtration and rinsed with water to give 29 g of crude title compound (76% yield). A 3.5-g portion of the solid was recrystallized twice from isopropyl alcohol/water and dried under high vaccum at 50° C. overnight to give 1.81 g of title compound, mp 225°-227° C.

Workup

  1. temperaturecooled
  2. temperaturethe solution was refluxed for an additional two hours
  3. filtrationfiltered into ice water (1 liter)
  4. customto give a solid which
  5. filtrationwas collected by filtration
  6. washrinsed with water
  7. customto give 29 g of crude title compound (76% yield)
  8. customA 3.5-g portion of the solid was recrystallized twice from isopropyl alcohol/water
  9. customdried under high vaccum at 50° C. overnight

Sources & evidence

ORD record
ord-e1d4f22914814768b3174483b8fa04f1
Source dataset
uspto-grants-1988_09
Patent number
US04772600

Reaction notes

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