Hydrochloric Acid → Am-211

HRID 2409525Notes

Reaction equation

HRID 2409525 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]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:36][CH3:37])[C:26]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)C.[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH2:29]([NH:28][C:26](=[O:27])[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:38])=[O:3])[CH:7]=1)[CH2:36][CH3:37])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66603809[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester

Product 1

HCID 44158492Am-211

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

[2′-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid ethyl ester (46.57 g) in THF (470 mL) and ethanol (370 mL) was treated with 1N aqueous NaOH (2 mL) for 45 minutes at room temperature. The mixture was acidified with 1N aqueous HCl (270 mL) and extracted three times with dichloromethane, the organics were dried with magnesium sulfate, filtered and concentrated, and the residue was purified by preparative HPLC to give [2′-(3-benzyl-1-ethyl-ureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialthe organics were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-898e929d751c4d55bc32f8e8326c8e7f
Source dataset
uspto-grants-2014_08
Patent number
US08815917B2

Reaction notes

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