Hydrochloric Acid → HCID 44538949, compound

HRID 1969019Notes

Reaction equation

HRID 1969019 reaction equation
C[O:2][C:3](=[O:35])[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:32](=[O:34])[CH3:33])[C:21]([CH3:31])([CH3:30])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:6]=1.[OH-].[Li+].Cl>C1COCC1>[C:32]([N:20]([CH2:19][C:13]1[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:12]=1[O:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:35])=[O:2])[CH:10]=[CH:9][CH:8]=1)[C:21]([CH3:30])([CH3:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58288507HCID 58288507, compound

Product 1

HCID 44538949HCID 44538949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To {3-[2-({acetyl-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethyl]-amino}-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester (0.094 g, 0.17 mmol) in THF (2 mL) was added 1N aqueous lithium hydroxide (2 mL), and the reaction was stirred at room temperature until no starting material was seen by analytical LCMS. 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 the title compound. M+H=529.

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-d6bf586e62e04460aea581d6730d2aea
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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