Sodium Hydroxide → HCID 11382331, compound

HRID 1693444Notes

Reaction equation

HRID 1693444 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:28])[C@@H:7]([NH:15][C:16]([C:18]1[NH:27][C:21]2=[CH:22][N:23]=[C:24]([Cl:26])[CH:25]=[C:20]2[CH:19]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C>C1COCC1>[Cl:26][C:24]1[CH:25]=[C:20]2[CH:19]=[C:18]([C:16]([NH:15][C@@H:7]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([OH:28])=[O:5])=[O:17])[NH:27][C:21]2=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11222505HCID 11222505, compound

Product 1

HCID 11382331HCID 11382331, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide solution (2.5 ml, 2M, 5.1 mmol) was added to a solution of 2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-phenylpropionic acid ethyl ester (EXAMPLE 41, 940 mg, 2.5 mmol) in THF (30 mL) and the reaction mixture was stirred at rt for 16 h. The solvent was removed in vacuo and the solid partitioned between hydrochloric acid (2M, 40 mL) and ethyl acetate (3×40 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid. m/z (ES+)=344 [M+H]+; RT=3.29 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid partitioned between hydrochloric acid (2M, 40 mL) and ethyl acetate (3×40 mL)
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e6e542156dcc497db991f7b9bd43edf3
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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