Sodium Hydroxide → HCID 68963289, compound

HRID 226430Notes

Reaction equation

HRID 226430 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10]1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86603733HCID 86603733, compound

Product 1

HCID 68963289HCID 68963289, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (2E)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (330 mg) and 1N NaOH solution (1.5 ml) in MeOH (30 ml) was stirred at 80-85° C. for 2 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture was AcOEt and H2O. The aqueous solution was adjusted to PH 5.4 with 5% HCl solution and resultant solution was evaporated in vacuo and the residue was dissolved in a MeOH and THF. The solvent was evaporated in vacuo and dried to give (2E)-3-(5-chloro-6-{[(3R)-1-(cyclohexylmethyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylic acid (306 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in a MeOH and THF
  5. customThe solvent was evaporated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-a3cb5bb6d89c480c9fbe917899655f0c
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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