Sodium Hydroxide → HCID 59753690, compound

HRID 1693484Notes

Reaction equation

HRID 1693484 reaction equation
C([O:3][C:4](=[O:27])[C@@H:5]([NH:14][C:15]([C:17]1[NH:26][C:20]2=[N:21][C:22]([Cl:25])=[CH:23][CH:24]=[C:19]2[CH:18]=1)=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C.[OH-].[Na+]>CO>[Cl:25][C:22]1[N:21]=[C:20]2[NH:26][C:17]([C:15]([NH:14][C@@H:5]([CH2:6][C:7]3[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=3)[C:4]([OH:27])=[O:3])=[O:16])=[CH:18][C:19]2=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59753760HCID 59753760, compound

Product 1

HCID 59753690HCID 59753690, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid ethyl ester (EXAMPLE 271, 780 mg, 2.0 mmol) in methanol (15 mL) was added 2M NaOH (2 mL, 4.0 mmol) and the reaction was stirred for 16 hr. Solvent was removed in vacuo and crude residue dissolved in water (20 mL). The aqueous phase was washed with ethyl acetate (2×20 mL), then acidified to Ph 3 with 2M HCl. The organics were extracted into ethyl acetate (2×30 mL), and then dried (MgSO4) before concentrating the solvent in vacuo to provide the title compound. m/z (ES+)=361.88 [M+H]+.

Workup

  1. customSolvent was removed in vacuo and crude residue
  2. dissolutiondissolved in water (20 mL)
  3. washThe aqueous phase was washed with ethyl acetate (2×20 mL)
  4. extractionThe organics were extracted into ethyl acetate (2×30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationbefore concentrating the solvent in vacuo

Sources & evidence

ORD record
ord-aca1fccec0d345a5ae6e279374d4c317
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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