Citric Acid → HCID 54672884, compound

HRID 563527Notes

Reaction equation

HRID 563527 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:38][CH3:39])[C:26]([NH:35][C:36]#[N:37])=[N:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O.CCOC(C)=O>[CH2:28]([N:27]=[C:26]([NH:35][C:36]#[N:37])[N:25]([CH2:24][C:15]1[CH:16]=[C:17]([C:20]([F:22])([F:23])[F:21])[CH:18]=[CH:19][C:14]=1[C:8]1[C:9]([O:12][CH3:13])=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:40])=[O:3])[CH:7]=1)[CH2:38][CH3:39])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 86651104HCID 86651104, compound

Product 1

HCID 54672884HCID 54672884, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

[2′-(N′-Benzyl-N″-cyano-N-ethyl-guanidinomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester (0.055 g, 0.1 mmol) in THF (2 mL) and H2O (0.5 mL) was treated with lithium hydroxide (0.02 g, 0.5 mmol), and the reaction was monitored by analytical LCMS. Once no starting material was seen, the mixture was diluted with EtOAc and H2O. Citric acid was added to neutralize the solution to pH 3, and the mixture was extracted with EtOAc. The combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated twice from CH2Cl2 to give the title compound. M+H is 525.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated twice from CH2Cl2

Sources & evidence

ORD record
ord-8629b69ea66a486cb0a05f7c1366fa24
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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