Citric Acid → HCID 16719111, compound

HRID 751445Notes

Reaction equation

HRID 751445 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-5d2fa9f7fb2f43e5841bd259e185d73e
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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