Acetic Acid → Ethanethioic acid trans-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

HRID 1290349ノート

反応式

HRID 1290349 の反応式
[OH:1][CH2:2][C@@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1.ClC(Cl)(Cl)[C:14]([N:16]=C=O)=[O:15].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.O1CCCC1.O>[NH2:16][C:14]([O:1][CH2:2][C@@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1)=[O:15]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 76400Trichloroacetyl isocyanateHCID 2724141Tetrabutylammonium FluorideHCID 15346553Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester

生成物 1

HCID 86752560Ethanethioic acid trans-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a -20° C. solution, under argon, of 0.406 g of product from Example 6 in 30 ml of methylene chloride is added 0.3 ml of trichloroacetyl isocyanate. The reaction is followed by thin layer chromatography (tlc). When reaction is complete, 1.16 ml of acetic acid, 0.54 ml of water and 9.84 ml of 1M tetrabutylammonium fluoride in tetrahydrofuran is added. The mixture is stirred at room temperature overnight followed by concentration in vacuo. The residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane) to give 0.430 g of the desired product.

後処理

  1. customWhen reaction
  2. concentrationfollowed by concentration in vacuo
  3. customThe residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-257d5a627116482c9d003c536f44e76d
出典データセット
uspto-grants-1998_05
特許番号
US05750735

反応ノート

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