Iodine → 1,2-Dithiolane

HRID 1881347노트

반응식

HRID 1881347 반응식
SC(S)C([N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]([CH2:9][OH:10])[CH2:7][OH:8])=O.[OH-].[Na+].II.[O-][S:24]([O-])(=[S:26])=O.[Na+].[Na+]>CCO.C(Cl)Cl>[S:24]1[CH2:16][CH2:14][CH2:17][S:26]1.[C:11]([NH:5][CH:6]([CH2:7][OH:8])[CH2:9][OH:10])([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12]

참가 물질

8

반응물 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 86640938HCID 86640938, 화합물

생성물 2

HCID 790451,2-DithiolaneHCID 10631565N-Boc-serinol

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

A solution of dimercaptoacetyl boc-serinol (4.1 mmol) in EtOH (20 ml) was treated with 10 ml of aqueous 1 N NaOH at room temperature for 1 h. The mixture was diluted with CH2Cl2 (100 ml) and then an aqueous solution of 0.1 M iodine (4.5 mmol) is added dropwise. The reaction mixture was stirred for 2 hours at room temperature and 1 mmol of Na2S2O3 (1 M aqueous solution) was added to the reaction mixture. The organic phase was separated, washed with water (3×200 mL), dried with magnesium sulfate, and evaporated at room temperature. The crude product was chromatographed on silica gel (200 mL) using a solvent mixture of hexane and ethyl acetate (40:20) as eluent to give 1,2-dithiolane of boc-serinol.

후처리

  1. customThe organic phase was separated
  2. washwashed with water (3×200 mL)
  3. dry with materialdried with magnesium sulfate
  4. customevaporated at room temperature
  5. customThe crude product was chromatographed on silica gel (200 mL)
  6. additiona solvent mixture of hexane and ethyl acetate (40:20) as eluent

출처 및 근거

ORD 기록
ord-705a5e0820cc41be94ac693a8f9f9842
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318795B2

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