Hydrochloric Acid → 4-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]amino]benzoic acid

HRID 1945404Notes

Reaction equation

HRID 1945404 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([NH:11][C:12](=[O:31])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]34[CH2:30][CH:25]5[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]5)[CH2:22]3)[CH2:28]4)=[CH:17][CH:16]=2)[CH:5]=1.[OH-].[K+].Cl>O1CCOCC1.O>[C:21]12([C:18]3[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:12]([NH:11][C:6]4[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=4[OH:10])[C:3]([OH:32])=[O:2])=[O:31])=[CH:16][CH:17]=3)[CH2:28][CH:27]3[CH2:29][CH:23]([CH2:24][CH:25]([CH2:26]3)[CH2:30]1)[CH2:22]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 16124726HCID 16124726, compound

Product 1

HCID 161247274-Hydroxy-3-[[2-(4-tricyclo[3.3.1.13,7]dec-1-ylphenoxy)acetyl]amino]benzoic acidYield 75.1%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (151.8 mg, 0.35 mmol) in 1,4-dioxane/H2O (10 ml) was treated with KOH (290.7 mg, 5.18 mmol) at 60° C. for 3 h. The reaction mixture was then acidified with 10% HCl to PH 2, and then partitioned between ethyl acetate and brine. The organic phase was washed with water, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2CH2:MeOH 4:1) to give 3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid as a white solid (110.4 mg, 75.10% yield).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash column chromatography (CH2CH2:MeOH 4:1)

Sources & evidence

ORD record
ord-54aa90ac923a43e9a8de754a20d08ac8
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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