Ethyl diazoacetate → 2-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-cyclopropanecarboxylic Acid Ethyl Ester

HRID 660643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660643
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[N-]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH2:37]([O:36][C:34]([CH:33]1[CH2:16][CH:15]1[C:13]1[CH:12]=[CH:11][C:10]([N:17]2[CH2:18][C:19](=[O:30])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[S:21]2(=[O:23])=[O:22])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)=[O:35])[CH3:38]

Komponenten

5

Edukt 2

HCID 12192Ethyl diazoacetateHCID 667565425-(2-Benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

Produkt 1

HCID 688399182-{3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-cyclopropanecarboxylic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 152122Dirhodium tetraacetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (Example 81, step A) (75 mg, 0.17 mmol) in methylene chloride is added rhodium acetate dimer (cat.). Ethyl diazoacetate (0.024 mL, 0.17 mmol) in methylene chloride (0.2 mL) is added dropwise via syringe pump over 4 h. The solvent is removed under reduced pressure and the crude material purified on silica gel using a gradient of 0-40% EtOAc/hexanes to give the title compound as a mixture of isomers (cis:trans 1:2) as a colorless oil: (M+H)+=548.

Aufarbeitung

  1. customThe solvent is removed under reduced pressure
  2. customthe crude material purified on silica gel using a gradient of 0-40% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8c40f294a41e4289aaae9ead84183b7b
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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