Citric Acid → HCID 16049866, compound

HRID 1713431Notes

Reaction equation

HRID 1713431 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-3e1fcc91e0424100a77310fe23b3c526
Source dataset
uspto-grants-2010_09
Patent number
US07795274B2

Reaction notes

Loading…