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

HRID 1020223Notes

Reaction equation

HRID 1020223 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 239619823-[(Pyridine-2-carbonyl)-amino]adamantane-1-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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, 2-11). ESI-MS m/z: 301.0 (M+H)+.

Workup

  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.

Sources & evidence

ORD record
ord-9d56d135bbcd4ded8b12f1f7ea59c498
Source dataset
uspto-grants-2014_05
Patent number
US08716284B2

Reaction notes

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