Sodium Hydroxide → Sodium 5-({3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}amino)-4-hydroxy-5-oxopentanoate

HRID 2218250Notes

Reaction equation

HRID 2218250 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17]([CH:19]3[CH2:23][CH2:22][C:21](=[O:24])[O:20]3)=[O:18])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:3]=1.[OH-:32].[Na+:33]>CO>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:18])[CH:19]([OH:32])[CH2:23][CH2:22][C:21]([O-:20])=[O:24])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:3]=1.[Na+:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135469510HCID 135469510, compound

Product 1

HCID 136114629Sodium 5-({3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}amino)-4-hydroxy-5-oxopentanoateYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide (0.250 g, 0.603 mmol) in methanol (10 mL) was added dropwise 2N NaOH solution (0.3 mL). After the mixture was stirred for 10 minutes, insoluble solid was filtered off. The filtrate was concentrated under reduced pressure and the residue was crystallized from methanol and ethyl ether. The resulting solid was collected by filtration under an argon atmosphere, washed with ethyl ether, and dried under reduced pressure to give Sodium 5-({3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}amino)-4-hydroxy-5-oxopentanoate as a pale yellow solid (0.165 g, yield 60%).

Workup

  1. filtrationinsoluble solid was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was crystallized from methanol and ethyl ether
  4. filtrationThe resulting solid was collected by filtration under an argon atmosphere
  5. washwashed with ethyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-c7188f09625f48aeb0a8a93e7c9f4126
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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