Hydrochloric Acid → (e)-[4-[3-(4-Chlorophenyl)-3-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]propynyl]phenyl]allyloxy]-2-methylphenoxy]acetic acid

HRID 549888Notes

Reaction equation

HRID 549888 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:25]2[CH:30]=[CH:29][C:28]([C:31]#[C:32][CH2:33][N:34]3[CH2:39][CH2:38][CH:37]([CH2:40][OH:41])[CH2:36][CH2:35]3)=[CH:27][CH:26]=2)=[CH:9]/[CH2:10][O:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20]C)=[O:19])=[C:14]([CH3:24])[CH:13]=2)=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl.[Cl-].[NH4+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](/[C:25]2[CH:26]=[CH:27][C:28]([C:31]#[C:32][CH2:33][N:34]3[CH2:35][CH2:36][CH:37]([CH2:40][OH:41])[CH2:38][CH2:39]3)=[CH:29][CH:30]=2)=[CH:9]/[CH2:10][O:11][C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:24])[CH:13]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 86629315HCID 86629315, compound

Product 1

HCID 57651518(e)-[4-[3-(4-Chlorophenyl)-3-[4-[3-[4-(hydroxymethyl)piperidin-1-yl]propynyl]phenyl]allyloxy]-2-methylphenoxy]acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The above ester (210 mg, 0.37 mmol) was dissolved in a mixture of tetrahydrofuran (5 mL) and methanol (2 mL). A solution of lithium hydroxide monohydrate (36 mg, 0.73 mmol) in water (2 mL) was added and the mixture was stirred for 2 h at ambient temperature. The reaction mixture was diluted with water (15 mL) and acidified with 2 M hydrochloric acid to pH˜6. A saturated solution of ammonium chloride (5 mL) was added and the mixture was extracted with ethyl acetate (4×15 mL). The organic extracts were washed with 10% aqueous solution of ammonium chloride (2×20 mL) and brine (2×15 mL), dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo. The residue was triturated with hexanes (2×10 mL) yielding the title compound as amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×15 mL)
  2. washThe organic extracts were washed with 10% aqueous solution of ammonium chloride (2×20 mL) and brine (2×15 mL)
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customsubsequently evaporated in vacuo
  5. customThe residue was triturated with hexanes (2×10 mL)

Sources & evidence

ORD record
ord-f6b1691336c64c6c8bda9516228b4065
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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