Citric Acid → HCID 16049866, compound

HRID 751447Notes

Reaction equation

HRID 751447 reaction equation
C([O:3][C:4](=[O:35])[C:5]([CH3:34])([CH3:33])[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)[C:8]=1[C:26](=[O:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])C.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC#N.CCOC(C)=O.O>[Cl:23][C:20]1[CH:21]=[CH:22][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)[C:8]([C:26](=[O:32])[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:7]2[CH2:6][C:5]([CH3:34])([CH3:33])[C:4]([OH:35])=[O:3])=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59754780HCID 59754780, compound

Product 1

HCID 16049866HCID 16049866, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

3-[1-(4-Chloro-benzyl)-3-(3,3-dimethyl-butyryl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (0.020 g, 0.04 mmol) was dissolved in MeCN (1 mL). 1N LiOH (0.16 mL, 0.16 mmol) was added and the reaction was heated to 60° C. overnight. 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. The crude material was purified by HPLC to give the desired acid. LCMS (ESI) M+H 471.

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
  7. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-2a47cbe544314fc8b3dab0aa8091767d
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

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