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

HRID 1290349노트

반응식

HRID 1290349 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-257d5a627116482c9d003c536f44e76d
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750735

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