TBAF tetrahydrofuran → 1-allyl-3-(S)-hydroxymethyl-4-(R)-phenylsulphonyl-2-azetidinone

HRID 65436

반응식

HRID 65436 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:45]([N:48]([CH2:54][S:55]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)(=[O:57])=[O:56])[C:49](=[O:53])[C@@H:50]1[O:52][CH2:51]1)[CH:46]=[CH2:47]>O1CCCC1>[CH2:45]([N:48]1[C@H:54]([S:55]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)(=[O:57])=[O:56])[C@@H:50]([CH2:51][OH:52])[C:49]1=[O:53])[CH:46]=[CH2:47]

참가 물질

5

반응물 3

HCID 11078149TBAF tetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 53927716N-allyl-N-phenylsulphonylmethyl-(R)-glycidic acid amide

생성물 1

HCID 186047761-allyl-3-(S)-hydroxymethyl-4-(R)-phenylsulphonyl-2-azetidinone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

8 ml of a tetra-n-butylammonium fluoride/THF solution which has been prepared from 5 g of tetra-n-butylammonium fluoride trihydrate by drying at 60°/0.1 torr and making up to 20.0 ml with tetrahydrofuran is added to a solution of 201 mg (0.757 mmol) of N-allyl-N-phenylsulphonylmethyl-(R)-glycidic acid amide in 1 ml of tetrahydrofuran. The resulting reaction mixture is stirred for 2 hours at 0° and then partitioned between methylene chloride and phosphate buffer solution having a pH of 8.0. The crude product isolated from the organic layer by means of concentration by evaporation is chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1) and the title compound is obtained in the form of a colourless oil.

후처리

  1. customby drying at 60°/0.1 torr
  2. customThe resulting reaction mixture
  3. custompartitioned between methylene chloride and phosphate buffer solution
  4. customThe crude product isolated from the organic layer by means of concentration by evaporation
  5. customis chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1)

출처 및 근거

ORD 기록
ord-ca824bbc1c4944458d3aa5974f6984c1
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04614614

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