Tetrahydrofuran → {Acetyl-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenyl]-amino}-acetic acid

HRID 547859Notes

Reaction equation

HRID 547859 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][N:6]([C:31](=[O:33])[CH3:32])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=3[O:29][CH3:30])=[CH:17][CH:16]=2)[CH:8]=1)C.O.[OH-].[Li+].O1CCCC1>O>[C:31]([N:6]([CH2:5][C:4]([OH:34])=[O:3])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([F:28])=[CH:23][C:22]=3[O:29][CH3:30])=[CH:19][CH:20]=2)[CH:8]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67153758{Acetyl-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenyl]-amino}-acetic acid ethyl ester

Product 1

HCID 52920348{Acetyl-[3-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-phenyl]-amino}-acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask containing {acetyl-[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenyl]-amino}-acetic acid ethyl ester (10 mg, 0.02 mmol) was added lithium hydroxide hydrate (2 mg, 0.05 mmol), tetrahydrofuran (0.5 mL) and water (0.5 mL). The reaction was stirred at room temperature overnight, diluted with ethyl acetated (25 mL) and washed with aqueous HCl (0.1 M, 25 mL) and brine (25 mL), dried over magnesium sulfate, concentrated and dried from hexanes/methylene chloride mixtures to yield {acetyl-[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenyl]-amino}-acetic acid as an off white solid (12 mg, 127%) LC-MS (ES) calculated for C24H21F2NO5, 441.14; found m/z 442 [M+H]+.

Workup

  1. additiondiluted with ethyl
  2. washwashed with aqueous HCl (0.1 M, 25 mL) and brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. dry with materialdried from hexanes/methylene chloride

Sources & evidence

ORD record
ord-fd45a76fe6e941f98acab9155f279e98
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Reaction notes

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