Hydrochloric Acid → HCID 44538951, compound

HRID 1969024Notes

Reaction equation

HRID 1969024 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][N:20]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1.[OH-].[Li+].Cl>C1COCC1.CO>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:7]2[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[CH:10]=[CH:9][CH:8]=2)=[C:13]([CH2:19][N:20]([C:29]([O:31][CH3:32])=[O:30])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58288494HCID 58288494, compound

Product 1

HCID 44538951HCID 44538951, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To (3-{4-bromo-2-[(methoxycarbonyl-phenethyl-amino)-methyl]-phenoxy}-phenyl)-acetic acid methyl ester in THF and MeOH was added lithium hydroxide, and the reaction was stirred overnight at room temperature. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc, and the combined organic layers were concentrated and purified by preparative HPLC to give the title compound. M+H=498.

Workup

  1. extractionextracted with EtOAc
  2. concentrationthe combined organic layers were concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-432f8dd0d7d345e4925270c52668f9a5
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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