Hydrochloric Acid → Am-211

HRID 2409521Notes

Reaction equation

HRID 2409521 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:24]([CH2:35][CH3:36])[C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[Li+].[OH-].Cl>C1COCC1>[CH2:28]([NH:27][C:25](=[O:26])[N:24]([CH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:21])([F:22])[F:20])[CH:17]=[CH:18][C:13]=1[C:7]1[C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]([CH2:4][C:3]([OH:37])=[O:2])[CH:6]=1)[CH2:35][CH3:36])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66604003[2'-(3-Benzyl-1-ethyl-ureidomethyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Product 1

HCID 44158492Am-211

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[2′-(3-benzyl-1-ethyl-ureidomethyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester (0.1 g) in THF (2 mL) was treated with 1N aqueous LiOH (2 mL) for 2 hours at room temperature. The mixture was acidified with 1N aqueous HCl and extracted three times with EtOAc. The combined organic layers were dried 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. M+H is 501.

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-3beddd03b43f4be0a4e3278aab743d9e
Source dataset
uspto-grants-2014_08
Patent number
US08815917B2

Reaction notes

Loading…