Hydrochloric Acid → HCID 52939613, compound

HRID 551498Notes

Reaction equation

HRID 551498 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:24]=4[O:31][CH3:32])=[CH:19][CH:18]=3)[CH:13]=2)[CH:8]=[N:7]1)C.O.[OH-].[Li+].CCOC(C)=O.Cl>C1COCC1.O>[F:30][C:26]1[C:27]([F:29])=[CH:28][C:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:15][C:12]3[CH:13]=[C:14]4[C:9]([CH:8]=[N:7][N:6]4[CH2:5][C:4]([OH:33])=[O:3])=[CH:10][CH:11]=3)=[CH:22][CH:21]=2)=[C:24]([O:31][CH3:32])[CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 67151458HCID 67151458, compound2×

Product 1

HCID 52939613HCID 52939613, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

[6-(4′,5′-Difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indazol-1-yl]-acetic acid ethyl ester (0.095 g, 0.204 mmol) and lithium hydroxide hydrate (10 mg, 0.245 mmol) in 5 mL THF/1 mL H2O was stirred at RT for 6 hrs. The reaction was distributed between EtOAc and H2O. The water layer was made acidic to pH 3 with 1N HCl and the organic layer was separated and concentrated in vacuo. The crude product was purified by trituration with Et2O to yield [6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indazol-1-yl]-acetic acid as a white solid. LC-MS (ES) calculated for C23H18F2N2O4, 424.41; found m/z 425 [M+H]+.

Workup

  1. customthe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by trituration with Et2O

Sources & evidence

ORD record
ord-41cc13d4ab4e42799671e938bf9a10d8
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

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