2-Methyl-2-butene → 5-(2-Acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid

HRID 2386176ノート

反応式

HRID 2386176 の反応式
[CH:1]([C:3]1[O:7][C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])=[CH:5][CH:4]=1)=[O:2].P([O-])([O-])([O-])=[O:19].[Na+].[Na+].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.C1COCC1.O>[C:14]([NH:13][C:11]1[S:12][C:8]([C:6]2[O:7][C:3]([C:1]([OH:19])=[O:2])=[CH:4][CH:5]=2)=[C:9]([CH3:17])[N:10]=1)(=[O:16])[CH3:15]

参加物

8

反応物 4

HCID 105532-Methyl-2-buteneHCID 24243Trisodium PhosphateHCID 14532745N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamideHCID 23668197Sodium Chlorite

生成物 1

HCID 593622035-(2-Acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1.2 g of N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamide in 100 mL of tert-butanol was added 5 mL of water and 20 mL of 2N monobasic sodium phosphate. The resulting suspension was cooled to 0° C. while being stirred. To the chilled suspension was added 20 mL of a 2M solution of 2-methyl-2-butene in THF followed by 3 g of sodium chlorite in 10 mL of water. The reaction was allowed to warm to room temperature overnight and the upper organic layer was separated and dried over sodium sulfate and used as is in the subsequent reactions. LC/MS: 267.04 (M+H)/2.04 min.

後処理

  1. temperatureto warm to room temperature overnight
  2. customthe upper organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. custom2.04 min.

出典と根拠

ORDレコード
ord-6710a48b72e7496ab71fcbd1057c37c5
出典データセット
uspto-grants-2012_09
特許番号
US08268818B2

反応ノート

読み込み中…