Citric Acid → HCID 16719111, compound

HRID 1713429Notes

Reaction equation

HRID 1713429 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH3:25])=[CH:12][CH:13]=2)[CH:8]=1)C.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CCOC(C)=O.O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:15]2[C:14]3[C:9](=[N:10][C:11]([O:24][CH3:25])=[CH:12][CH:13]=3)[CH:8]=[C:7]2[CH2:6][C:5]([CH3:27])([CH3:26])[C:4]([OH:28])=[O:3])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 59754773HCID 59754773, compound

Product 1

HCID 16719111HCID 16719111, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

3-[5-Methoxy-1-(4-chloro-benzyl)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (0.050 g, 0.12 mmol) was dissolved in THF (0.1 mL), MeOH (0.1 mL), and H2O (0.1 mL). LiOH (0.02 g, 0.50 mmol) was added and the reaction was heated to 60° C. for 2 hours. Once no starting material was seen by LCMS, the reaction was cooled to room temperature and diluted with EtOAc and water. The mixture was neutralized with solid citric acid to pH 5, the aqueous layer was extracted three times with EtOAc, the combined organics were washed twice with water, once with brine, dried over MgSO4, filtered and concentrated to give the desired acid. LCMS (ESI) M+H 373.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionthe aqueous layer was extracted three times with EtOAc
  3. washthe combined organics were washed twice with water, once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f82d719f2f0d4390aa697de46460bd7f
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

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