2-Methoxybenzaldehyde → HCID 58609897、化合物

HRID 408498

反応式

HRID 408498 の反応式
C([Li])CCC.[CH2:6]([O:8][C:9]([C:11]1[N:12]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:14][CH:15]=1)=[O:10])[CH3:7].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>O1CCCC1>[CH2:6]([O:8][C:9]([C:11]1[N:12]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[S:14][C:15]=1[CH:28]([OH:29])[C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=1[O:25][CH3:24])=[O:10])[CH3:7]

参加物

5

反応物 3

HCID 86582-MethoxybenzaldehydeHCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 58609897HCID 58609897、化合物収率 48.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Butyl lithium (2.5 M, 53 mL, 132 mmol) was slowly added to a solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid ethyl ester (16.4 g, 60 mmol) in anhydrous tetrahydrofuran (250 mL) at −78° C. under a nitrogen atmosphere. A solution of 2-methoxybenzaldehyde (10.89 g, 79.99 mmol) in tetrahydrofuran (50 mL) was then added dropwise at −78° C. The mixture was warmed slowly to room temperature and stirred for 15 hours. The reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (500 mL). The separated aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness. The crude product was then purified by column chromatography to yield the pure product (12 g, 29 mmol, 48%).

後処理

  1. customThe reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (500 mL)
  2. extractionThe separated aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was then purified by column chromatography

出典と根拠

ORDレコード
ord-751f3845f70c4c01b100c125cac34ad4
出典データセット
uspto-grants-2014_06
特許番号
US08759335B2

関連ノート

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