1,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl- → HCID 178464540、化合物

HRID 417800

反応式

HRID 417800 の反応式
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[NH2:5].[CH3:14][C:15]([CH:17]1[C:23](=[O:24])[CH2:22][C:21]([CH3:26])([CH3:25])[CH2:20][C:18]1=[O:19])=O>CO>[CH3:26][C:21]1([CH3:25])[CH2:22][C:23](=[O:24])[C:17](=[C:15]([NH:5][C@@H:4]2[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([CH2:12][OH:13])[O:11][C@@H:3]2[OH:2])[CH3:14])[C:18](=[O:19])[CH2:20]1

参加物

4

反応物 2

HCID 5194481,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl-HCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

生成物 1

HCID 178464540HCID 178464540、化合物収率 188.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Glucosamine hydrochloride (50 g, 231 mmol) was suspended in anhydrous methanol (500 mL), then 2-acetyl-dimedone sodium salt (47.3 g, 231 mmol) was added. The reaction mixture was stirred at room temperature for 10 minutes, then 2-acetyl-dimedone (21.1 g, 115.9 mmol) was added. The reaction mixture was stirred under reflux for 2.5 hours and monitored by tlc. At the completion of the reaction (TLC: MeCN—H20, 10:2), the reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated and the resulting solid residue was washed on a funnel with ether (3×500 mL) and dried to give crude product (75 g, 94%). No further purification was required for the next reaction.

後処理

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 2.5 hours
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. washthe resulting solid residue was washed on a funnel with ether (3×500 mL)
  7. customdried

出典と根拠

ORDレコード
ord-c8cb6b6bdd17431cbaedc4f6bae64cec
出典データセット
uspto-grants-2012_01
特許番号
US08093227B2

関連ノート

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