Potassium Hydroxide → HCID 16656998, compound

HRID 1445938Notes

Reaction equation

HRID 1445938 reaction equation
[NH2:1][C:2](=[O:34])[C:3]([C:5]1[C:9]2[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[N:11][CH:12]=[CH:13][C:8]=2[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2C2C=CC=CC=2)[C:6]=1[CH2:32][CH3:33])=[O:4].[OH-].[K+].O.[OH-].[Li+]>CO.O>[NH2:1][C:2](=[O:34])[C:3]([C:5]1[C:9]2[C:10]([O:14][CH2:15][C:16]([OH:18])=[O:17])=[N:11][CH:12]=[CH:13][C:8]=2[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]=1[CH2:32][CH3:33])=[O:4]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 16656999HCID 16656999, compound

Product 1

HCID 16656998HCID 16656998, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-(3-(2-amino-2-oxoacetyl)-1-(biphenyl-2-ylmethyl)-2-ethyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)acetic acid, Ily-II-10: Compound 21 (0.227 mmol) is dissolved in methanol (20 mL). To the mixture the solution of KOH (1M, 0.25 mL) is added at room temperature. After addition the mixture was stirred at room temperature for 18 h. Then solution of lithium hydroxide monohydrate (90 mg) in H2O (5 mL) is added. After another hour stirring the mixture was concentrated and the residue is redissolved in methanol (10 mL) and ethanol (10 mL). The mixture is filtered and the filtrate was acidified by hydrogen chloride in ether (1.0 M) to pH=3-4. Solvent is evaporated and the residue is washed with a mixture of dichloromethane: ether (1:1), then water (5 mL) and ether to afford 2-(3-(2-amino-2-oxoacetyl)-1-benzyl-2-ethyl-1H-pyrrolo[3,2-c]pyridin-4-yloxy)acetic acid, Ily-II-10.

Workup

  1. additionAfter addition the mixture
  2. stirringAfter another hour stirring the mixture
  3. concentrationwas concentrated
  4. dissolutionthe residue is redissolved in methanol (10 mL)
  5. filtrationThe mixture is filtered
  6. customSolvent is evaporated
  7. washthe residue is washed with a mixture of dichloromethane: ether (1:1)

Sources & evidence

ORD record
ord-2147629e687b4b29b1a1929c77e22542
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

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