Water → HCID 14390428, compound

HRID 1709584Notes

Reaction equation

HRID 1709584 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 (250 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 acidified 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 vacuum 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 vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-0648c1c452d34e2090017fd171d3541f
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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