Nitrogen → HCID 54537147, Verbindung

HRID 865455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865455
CCN(CC)CC.[CH3:8][S:9](Cl)(=O)=O.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:27]=1)O)(=[O:15])[CH3:14].C([O-])(O)=O.[Na+].S([O-])(=O)(=O)C.S[CH2:51][CH:52](C)[C:53]([O:55][CH2:56][CH3:57])=[O:54].C([O-])([O-])=O.[Cs+].[Cs+].N#N>C(Cl)Cl.CC#N>[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH:24]([S:9][CH2:8][CH:52]([CH3:51])[C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:27]=1)(=[O:15])[CH3:14]

Komponenten

11

Edukt 8

HCID 947NitrogenHCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 15289599Ethyl 3-mercapto-2-methylpropanoateHCID 53725555HCID 53725555, Verbindung

Produkt 1

HCID 54537147HCID 54537147, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

At -40° C., Et3N (triethylamine) (1.60 mL, 11.5 mmol) and methanesulfonyl chloride (750 μl, 9.69 mmol) were added to a solution of the alcohol of Step 6 (7.39 mmol) in 74 mL of CH2Cl2 and the mixture was stirred at -40° C. for an hour and at -10° C. for 45 minutes. Saturated aq NaHCO3 was then added and the mesylate was extracted with CH2Cl2, dried over Na2SO4 and concentrated. To this mesylate in 150 mL of anhydrous CH3CN, ethyl 3-mercapto-2-methylpropanoate (Example 4, Step 6; 2.20 mL, approx. 15 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were added and the mixture was stirred under a stream of N2 for 2 hours. 25% Aq NH4OAc was then added and the title product was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene.

Aufarbeitung

  1. extractionthe mesylate was extracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. extractionthe title product was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography on silica with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-18d0c96fb0a44dfd8f0d713564a6e57c
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565473

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