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Hydrochloric Acid → (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

HRID 329675
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HRID 329675 반응식
[Si]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:25])[C:16](=[O:24])[CH2:17][C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[NH:13][C:12]1=[O:26])[CH3:10])(C(C)(C)C)(C)C.Cl.OP([O-])([O-])=O.[K+].[K+]>CO.C(OC(=O)C)C.O>[OH:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@@H:15]([CH3:25])[C:16](=[O:24])[CH2:17][C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[NH:13][C:12]1=[O:26])[CH3:10]
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참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 24450Potassium Phosphate, DibasicHCID 14138755(3S,4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

생성물 1

HCID 14329059(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone수율 89%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

실험 절차

The keto ester 2 (1.047 g, 2.73 mmol) in methanol (12.3 ml) was treated with 6N HCl (1.37 ml, 8.22 mmol, 3 eg) and stirred 1 hour at room temperature. The solution was treated with 1M K2HPO4 (8.2 ml) and stirred a few minutes, then diluted with ethylacetate and water. The organic layer was separated, washed with 5% NaHCO3 and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to give the product 3 (0.653 g, 89%) as a clear oil.

후처리

  1. stirringstirred a few minutes
  2. customThe organic layer was separated
  3. washwashed with 5% NaHCO3 and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-0ae4142789d4493380135c93e84eb8fa
출처 데이터셋
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04892869

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