Hydrochloric Acid → AM-432

HRID 1625676Notes

Reaction equation

HRID 1625676 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=3)=[CH:16][C:15]=2[CH2:29][N:30]([C:33]([CH:35]2[CH2:37][CH2:36]2)=[O:34])[CH2:31][CH3:32])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[OH-].[Li+].Cl>O1CCCC1.O>[CH:35]1([C:33]([N:30]([CH2:29][C:15]2[CH:16]=[C:17]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=3)[CH:18]=[CH:19][C:14]=2[C:8]2[C:9]([O:12][CH3:13])=[CH:10][CH:11]=[C:6]([CH2:5][C:4]([OH:38])=[O:3])[CH:7]=2)[CH2:31][CH3:32])=[O:34])[CH2:36][CH2:37]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58149167[2'-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4'-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester

Product 1

HCID 50901658AM-432

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[2′-[(cyclopropanecarbonyl-ethyl-amino)-methyl]-4′-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester (32.7 g, 63.3 mmol) in tetrahydrofuran (150 mL) and water (75 mL) was treated with lithium hydroxide (8.0 g, 190.6 mmol) and the reaction was stirred at room temperature overnight. When the reaction was complete by analytical LCMS, the mixture was acidified with 1N aqueous hydrochloric acid to pH 3 and extracted 2 times with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated to afford the title compound as an off-white foam.

Workup

  1. extractionextracted 2 times with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea2a4e78adc344fd810e08c935200fe2
Source dataset
uspto-grants-2014_07
Patent number
US08785393B2

Reaction notes

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