Tetrahydrofuran → (3S,4R)-3-[1-(R)-t-Butyldimethylsilyloxyethyl]-4-(2-p-nitrobenzyloxycarbonylaminoethyl)thiomethylcarbonylmethylazetidin-2-one

HRID 355009

반응식

HRID 355009 반응식
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][O:9][C:10]([NH:12][CH2:13][CH2:14][SH:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:19][C:20]([CH2:22][C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1[C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH3:29])=[O:21].O1CCCC1.C([Li])CCC>CCCCCC.C(OCC)(=O)C.C(O)(=O)C>[Si:31]([O:30][C@@H:28]([C@@H:24]1[C@@H:23]([CH2:22][C:20]([CH2:19][S:15][CH2:14][CH2:13][NH:12][C:10]([O:9][CH2:8][C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])=[O:21])[NH:26][C:25]1=[O:27])[CH3:29])([C:34]([CH3:37])([CH3:35])[CH3:36])([CH3:33])[CH3:32]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 3017625(4-Nitrophenyl)methyl (2-mercaptoethyl)carbamateHCID 14166264(3S,4R)-4-Bromomethylcarbonylmethyl-3-[1-(R)-t-butyldimethylsilyloxyethyl]-azetidin-2-oneHCID 178418339Butyllithium

생성물 1

HCID 70528790(3S,4R)-3-[1-(R)-t-Butyldimethylsilyloxyethyl]-4-(2-p-nitrobenzyloxycarbonylaminoethyl)thiomethylcarbonylmethylazetidin-2-one수율 76.3%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

0.536 g. of 2-(p-nitrobenzyloxycarbonylamino)ethylmercaptan was added to a mixture of 0.635 g. of bromomethylazetidin-2-one (48) and 20 ml. of dry tetrahydrofuran. The mixture was cooled to -78° C. and a solution of 1.18 ml of n-butyllithium in n-hexane was added thereto. The mixture was stirred at that temperature for 1.5 hours. Acetic acid (0.22 ml) was added to the reaction mixture. The mixture was then diluted with 380 ml of ethyl acetate and washed successively with water and an aqueous solution of sodium chloride, and was then dried over sodium sulphate. The solvent was distilled off under reduced pressure and the resulting oily residue was subjected to rapid chromatography using silica gel eluted with a 1:4 by volume mixture of benzene and ethyl acetate, to afford 0.718 g. (yield 76.3%) of the desired azetidin-2-one (49).

후처리

  1. washwashed successively with water
  2. dry with materialan aqueous solution of sodium chloride, and was then dried over sodium sulphate
  3. distillationThe solvent was distilled off under reduced pressure
  4. washeluted with a 1:4 by volume mixture of benzene and ethyl acetate
  5. customto afford 0.718 g

출처 및 근거

ORD 기록
ord-efe42f79f3824da1b6d88591d90be46c
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377591

연결된 노트

불러오는 중…