Acetic Acid → allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464735노트

반응식

HRID 1464735 반응식
[Si]([O:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[C@@H:12]1[C@@H:13]([CH3:27])[C:14]([S:25][CH3:26])=[C:15]2[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[C@@H:12]1[C@@H:13]([CH3:27])[C:14]([S:25][CH3:26])=[C:15]2[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

생성물 1

HCID 57069192allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate수율 80.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) was added to a mixture of 70% aqueous tetrabutylammonium fluoride (0.71 g) and acetic acid (121 mg) in tetrahydrofuran (2 ml) and the mixture was allowed to stand at ambient temperature for 24 hours. The solution was diluted with ethyl acetate (6 ml), washed with water, aqueous sodium bicarbonate solution and brine, and dried. The solvent was removed off under reduced pressure and the residue was crystallized from n-hexane to afford allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (58.4 mg).

후처리

  1. washwashed with water, aqueous sodium bicarbonate solution and brine
  2. customdried
  3. customThe solvent was removed off under reduced pressure
  4. customthe residue was crystallized from n-hexane

출처 및 근거

ORD 기록
ord-ad500ece2b014042ad68262e46bb326a
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306816

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