Hydrochloric Acid → HCID 68993903, compound

HRID 1945406Notes

Reaction equation

HRID 1945406 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH2:5][C:6]([NH:14][C:15](=[O:34])[CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]34[CH2:33][CH:28]5[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]5)[CH2:25]3)[CH2:31]4)=[CH:20][CH:19]=2)([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9]C)=[O:8].Cl>O1CCOCC1.O>[C:24]12([C:21]3[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:15]([NH:14][C:6]4([C:7]([OH:9])=[O:8])[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:35])=[O:2])[CH2:5]4)=[O:34])=[CH:19][CH:20]=3)[CH2:33][CH:28]3[CH2:27][CH:26]([CH2:32][CH:30]([CH2:29]3)[CH2:31]1)[CH2:25]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68995126HCID 68995126, compound

Product 1

HCID 68993903HCID 68993903, compoundYield 105.3%

Reagents, catalysts & solvents 1

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

Procedure

A 3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-isophthalic acid dimethyl ester (158.9 mg, 0.34 mmol) in 1,4-dioxane/H2O (1:1, 3.5 ml) was treated with LiOHH2O (56.2 mg, 1.34 mmol) at room temperature. 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=5:1) to give 3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-isophthalic acid as a white solid (161.7 mg, 100% 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=5:1)

Sources & evidence

ORD record
ord-12d064c86ed34fa38361a78213cb6816
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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