Tetrahydrofuran → 3-[(Pyridine-2-carbonyl)-amino]adamantane-1-carboxylic acid

HRID 218020

Reaktionsgleichung

Reaktionsgleichung von HRID 218020
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([NH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[O:17])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].O1CCCC1.O.[OH-].[Li+]>O>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]([NH:15][C:7]12[CH2:13][CH:11]3[CH2:10][CH:9]([CH2:14][C:5]([C:3]([OH:4])=[O:2])([CH2:12]3)[CH2:6]1)[CH2:8]2)=[O:17]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 497204493-[(Pyridine-2-carbonyl)-amino]adamantane-1-carboxylic acid methyl ester

Produkt 1

HCID 239619823-[(Pyridine-2-carbonyl)-amino]adamantane-1-carboxylic acidAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a round bottom flask was added 3-[(pyridine-2-carbonyl)-amino]-adamantane-1-carboxylic acid methyl ester (24.8 g, 78.9 mmol), tetrahydrofuran (250 mL), water (250 mL) and lithium hydroxide monohydrate (14.9 g, 355 mmol) and the mixture was stirred vigorously at room temperature for 25 hours. The crude mixture was concentrated under reduced pressure to remove most of the tetrahydrofuran, then the aqueous solution was diluted with water (200 mL) and the pH was adjusted to about 3-4 by adding solid citric acid monohydrate. A voluminous white precipitate appeared which was filtered, washed with water and dried under high vacuum at 50° C. to afford 22.1 g (93%) of the title compound, 3-[(pyridine-2-carbonyl)-amino]-adamantane-1-carboxylic acid, as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.55-8.50 (m, 1H), 8.18 (d, J=7.7 Hz, 1H), 7.97 (br s, 1H), 7.85 (td, J=7.8, 1.8 Hz, 1H), 7.42 (ddd, J=7.6, 4.8, 1.3 Hz, 1H), 2.35-2.31 (m, 2H), 2.31-2.25 (m, 2H), 2.25-2.09 (m, 4H), 2.00-1.86 (m, 4H), 1.80-1.64 (m, 2H). ESI-MS m/z: 301.0 (M+H)+.

Aufarbeitung

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. customto remove most of the tetrahydrofuran
  3. additionthe aqueous solution was diluted with water (200 mL)
  4. additionby adding solid citric acid monohydrate
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried under high vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-a1b9ba15a0da4da0a977724591dde9f7
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198275B2

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