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

HRID 65436

反応式

HRID 65436 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ca824bbc1c4944458d3aa5974f6984c1
出典データセット
uspto-grants-1986_09
特許番号
US04614614

関連ノート

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