Lithium Hydroxide → 3-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid

HRID 2089540

反応式

HRID 2089540 の反応式
C[O:2][C:3]([C:5]1[N:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)[CH:7]=[N:8][CH:9]=1)=[O:4].[Li+].[OH-]>C(O)C>[CH:10]1([N:6]2[C:5]([C:3]([OH:4])=[O:2])=[CH:9][N:8]=[CH:7]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 144976243-(1,2,3,4-Tetrahydronaphthalen-1-YL)-3H-imidazole-4-carboxylic acid methyl ester

生成物 1

HCID 197940793-(1,2,3,4-Tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid methyl ester, which can be prepared as described in Example 2, (0.510 g, 1.990 mmol) in ethanol (20 mL) is added aqueous 4M LiOH (5 mL, 20 mmol) causing an immediate precipitate to form. After 3 hours, the mixture is evaporated to dryness, re-dissolved in a minimum amount of water, and the pH is adjusted to 6 with aqueous 2M HCl, causing a precipitate to form. The reaction is cooled to 0° C. and allowed to stand for 30 minutes. The precipitate is then filtered off and washed with cold phosphate buffer (pH 6). Upon standing, a solid precipitates out of the phosphate buffer which is filtered and combined with the initial precipitate to yield, upon drying under high vacuum, 3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid; MS: (ESI) m/z 243.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.77-1.96 (m, 2 H), 2.21-2.36 (m, 2 H), 2.87-2.95 (m, 1 H), 3.05 (dt, J=16.9, 5.8 Hz, 1 H), 6.57 (t, J=5.6 Hz, 1 H), 7.01 (d, J=7.8 Hz, 1 H), 7.18-7.26 (m, 1 H), 7.26-7.36 (m, 2 H), 7.55 (s, 1 H), 7.79 (d, J=1.0 Hz, 1 H).

後処理

  1. customto form
  2. customthe mixture is evaporated to dryness
  3. dissolutionre-dissolved in a minimum amount of water
  4. customto form
  5. waitto stand for 30 minutes
  6. filtrationThe precipitate is then filtered off
  7. washwashed with cold phosphate buffer (pH 6)
  8. customa solid precipitates out of the phosphate buffer which
  9. filtrationis filtered
  10. customto yield
  11. dry with materialupon drying under high vacuum, 3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid

出典と根拠

ORDレコード
ord-84abd9f4012342cfa487636a6fefcd25
出典データセット
uspto-grants-2013_05
特許番号
US08436035B2

関連ノート

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