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

HRID 1945403

Reaktionsgleichung

Reaktionsgleichung von HRID 1945403
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 39672954-[2-(4-Adamantan-1-yl-phenoxy)acetylamino]-benzoic acidAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e40c1d2c7fd14a95808a0b1f05c3c747
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394799B2

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