Hydrochloric Acid → HCID 45138630, compound

HRID 554632Notes

Reaction equation

HRID 554632 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH2:22][N:23]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]([CH:26]2[CH2:28][CH2:27]2)=[O:25])[CH:11]=1)C.[Li+].[OH-].Cl>C1COCC1.CO>[CH2:29]([N:23]([CH2:22][C:13]1[CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=[CH:17][C:12]=1[C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:36])=[O:3])[CH:7]=[N:8][CH:9]=1)[C:24]([CH:26]1[CH2:28][CH2:27]1)=[O:25])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67212487HCID 67212487, compound

Product 1

HCID 45138630HCID 45138630, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (5-{2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.043 g, 0.09 mmol) in THF (3 mL) and MeOH (0.3 mL) was added 1N aqueous LiOH (3 mL), and the reaction was stirred at room temperature. The mixture was neutralized with 1N aqueous HCl to pH 4-5 and extracted three times with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by preparative HPLC to give Compound 17.

Workup

  1. extractionextracted three times with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-be3623fa74c44e2a88ab19ae62c09225
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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