Hydrochloric Acid → 2-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid

HRID 1945402Notes

Reaction equation

HRID 1945402 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:30])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]23[CH2:29][CH:24]4[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]4)[CH2:21]2)[CH2:27]3)=[CH:16][CH:15]=1.Cl.C(OCC)(=O)C>O1CCOCC1.O>[C:20]12([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:31])=[O:2])=[O:30])=[CH:15][CH:16]=3)[CH2:29][CH:24]3[CH2:23][CH:22]([CH2:28][CH:26]([CH2:25]3)[CH2:27]1)[CH2:21]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 161250652-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester

Product 1

HCID 42163142-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acidYield 65.2%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 2-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester (30.5 mg, 0.07 mmol) in 1,4-dioxane/H2O (3:1, 3 mL) added LiOHH2O (8.4 mg, 0.2 mmol) at room temperature. The resulting mixture was stirred overnight, and then acidified with 10% HCl to PH 2. Ethyl acetate was added and the organic layer was separated. The organic layer was washed with water, and dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:EtOAc:MeOH=6:3:1) to gave 2-[2-(4-Adamant-1-yl-phenoxy)-acetylamino]-benzoic acid as a white solid (18.5 mg, 62.5% yield).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4 anh)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash column chromatography (n-Hexane:EtOAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-7b88b9fb0e174892be5bfcf98fb6062f
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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