Hydrochloric Acid → HCID 68602961, compound

HRID 1486012Notes

Reaction equation

HRID 1486012 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Br:16])=[CH:11][C:10]=1[C:17](=[O:28])[N:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])[CH3:19])C(OC)=O.O[Li].O.Cl>C1COCC1.O>[Br:16][C:12]1[C:13]([Cl:15])=[CH:14][C:9]([CH2:4][C:3]([OH:29])=[O:2])=[C:10]([C:17](=[O:28])[N:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH3:19])[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68602143HCID 68602143, compound

Product 1

HCID 68602961HCID 68602961, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-{4-bromo-5-chloro-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenyl}-malonic acid dimethyl ester (1.4 g, 2.8 mmol) and LiOH.H2O (0.7 g, 16.7 mmol) was stirred at 60° C. in a mixture of THF (20 mL) and water (2 mL) for 24 hrs, then acidified by 1N HCl to pH 4. The mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and brine, and was dried over MgSO4. The filtrate was then concentrated and purified by silica gel flash column chromatography eluting with 10% MeOH in DCM to yield 2-{4-bromo-5-chloro-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenyl}-acetic acid (427 mg). MS: [M+H]+ 413.9/412.0; tR=2.60 min (method 1)

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was then washed with water and brine
  3. dry with materialwas dried over MgSO4
  4. concentrationThe filtrate was then concentrated
  5. custompurified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in DCM

Sources & evidence

ORD record
ord-96615e776c904990a73e6dc868c5e7db
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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