Citric Acid → HCID 68698989, compound

HRID 1865174Notes

Reaction equation

HRID 1865174 reaction equation
C([C:3]1[C:4]([N:15]2[CH2:19][CH2:18][C@@H:17]([C:20]3([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:21]3)[CH2:16]2)=[C:5]([O:13][CH3:14])[C:6]([F:12])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:27]([O:26][C:24]([NH:23][C:20]1([C@@H:17]2[CH2:18][CH2:19][N:15]([C:4]3[CH:3]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:12])[C:5]=3[O:13][CH3:14])[CH2:16]2)[CH2:22][CH2:21]1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86605362HCID 86605362, compound

Product 1

HCID 68698989HCID 68698989, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4-[(3R)-3-(1-tert.-butoxycarbonylaminocyclopropyl)-pyrrolidin-1-yl]-2-fluoro-3-methoxybenzoic acid (3.61 g) was dissolved in 28 mL of ethanol, 1N aqueous sodium hydroxide solution (34.5 mL) was added to the solution, and the mixture was heated to 50° C. with stirring. After completion of the reaction, 10% aqueous citric acid solution was added to the mixture followed by extraction with chloroform. An organic layer was dried with anhydrous sodium sulfate and filtered, and then the solvent was distilled away. The title compound was obtained as residual crystals (4.45 g). The crystals were used in the next step without purification.

Workup

  1. additionwas added to the mixture
  2. extractionfollowed by extraction with chloroform
  3. dry with materialAn organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-99ac952f0bcf47e6bb09687132447c0d
Source dataset
uspto-grants-2009_12
Patent number
US07626029B2

Reaction notes

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