Sodium Iodide → HCID 68283670, Verbindung

HRID 1527429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527429
[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][C@:11]2([CH2:17]OS(C)(=O)=O)[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[I-].CO[CH2:27][CH2:28]OC>[Zn]>[CH2:27]([O:16][C:14]([C@@H:13]1[CH2:12][C@:11]2([CH3:17])[C@@H:9]([CH2:10]2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:15])[CH3:28]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 80711,2-DimethoxyethaneHCID 86673856HCID 86673856, Verbindung

Produkt 1

HCID 68283670HCID 68283670, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

To a solution of (1R,3S,5S)-5-methanesulfonyloxymethyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (100 mg, 0.24 mmol) in DME (2.6 mL) were successively added NaI (355 mg, 2.37 mmol) and zinc powder (155 mg, 2.37 mmol). The reaction mixture was refluxed 30 min under argon atmosphere, cooled to RT and quenched by addition of a saturated aqueous solution of NH4Cl (1.6 mL). CH2Cl2 (1.6 mL) and few Na2S crystals were added and the biphasic mixture was stirred at RT for 1 h. The layers were separated, the organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (eluent: c-hexane to c-hexane/EtOAc). TLC, Rf (c-hexane/EtOAc 2:1)=0.60; MS (UPLC/MS): 270.3 [M+H]+, 214.2 [MH−tBu]+, 170.2 [MH−Boc]+; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 4.11 (m, 2H), 3.95 (m, 1H), 3.10 (m, 1H), 2.42 (m, 1H), 1.84 (m, 1H), 1.38 (m, 9H), 1.20 (t, 3H), 1.18 (s, 3H) 0.69 (dd, 1H), 0.64 (m, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed 30 min under argon atmosphere
  2. customquenched by addition of a saturated aqueous solution of NH4Cl (1.6 mL)
  3. additionCH2Cl2 (1.6 mL) and few Na2S crystals were added
  4. customThe layers were separated
  5. washthe organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by flash column chromatography on silica gel (eluent: c-hexane to c-hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0d9430caab7b4ccab155ecebec3737a3
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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