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

HRID 1945403Notes

Reaction equation

HRID 1945403 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]5)[CH2:21]3)[CH2:27]4)=[CH:16][CH:15]=2)=[CH:6][CH:5]=1.Cl>O1CCOCC1.O>[C:20]12([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:7]4[CH:6]=[CH:5][C:4]([C:3]([OH:31])=[O:2])=[CH:9][CH:8]=4)=[O:30])=[CH:15][CH:16]=3)[CH2:27][CH:26]3[CH2:28][CH:22]([CH2:23][CH:24]([CH2:25]3)[CH2:29]1)[CH2:21]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3470321Methyl 4-({[4-(1-adamantyl)phenoxy]acetyl}amino)benzoate

Product 1

HCID 39672954-[2-(4-Adamantan-1-yl-phenoxy)acetylamino]-benzoic acidYield 62.7%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 4-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid methyl ester (79.1 mg, 0.16 mmol) in 1,4-dioxane/H2O (3:1, 8 ml) was treated with LiOHH2O (15.9 mg, 0.38 mmol) at room temperature until the reaction was complete, as judged by TLC. 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 (n-Hexane:EtoAc:MeOH=6:3:1) to give 4-[2-(4-Adamantan-1-yl-phenoxy)acetylamino]-benzoic acid as a white solid (40.7 mg, 53.1% 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 (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-e40c1d2c7fd14a95808a0b1f05c3c747
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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