1,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl- → HCID 178464540, 화합물

HRID 417800

반응식

HRID 417800 반응식
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

참가 물질

4

반응물 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

생성물 1

HCID 178464540HCID 178464540, 화합물수율 188.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c8cb6b6bdd17431cbaedc4f6bae64cec
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093227B2

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