Potassium Carbonate → 17-Allyl-12-[2-(4-tert-butyl-diphenylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2,3,10,16-tetraone

HRID 1532411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532411
C(O[CH:5]1[CH2:31][C:30](=[O:32])[CH:29]([CH2:33][CH:34]=[CH2:35])[CH:28]=[C:27]([CH3:36])[CH2:26][CH:25]([CH3:37])[CH2:24][CH:23]([O:38][CH3:39])[CH:22]2[O:40][C:18]([OH:44])([CH:19]([CH3:43])[CH2:20][CH:21]2[O:41][CH3:42])[C:17](=[O:45])[C:16](=[O:46])[N:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:47])[O:8][CH:7]([C:48]([CH3:76])=[CH:49][CH:50]2[CH2:55][CH2:54][CH:53]([O:56][Si:57]([C:70]([CH3:73])([CH3:72])[CH3:71])([C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH:52]([O:74][CH3:75])[CH2:51]2)[CH:6]1[CH3:77])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)C>[CH2:33]([CH:29]1[CH:28]=[C:27]([CH3:36])[CH2:26][CH:25]([CH3:37])[CH2:24][CH:23]([O:38][CH3:39])[CH:22]2[O:40][C:18]([OH:44])([CH:19]([CH3:43])[CH2:20][CH:21]2[O:41][CH3:42])[C:17](=[O:45])[C:16](=[O:46])[N:15]2[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[C:9](=[O:47])[O:8][CH:7]([C:48]([CH3:76])=[CH:49][CH:50]2[CH2:55][CH2:54][CH:53]([O:56][Si:57]([C:70]([CH3:73])([CH3:72])[CH3:71])([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[CH:52]([O:74][CH3:75])[CH2:51]2)[CH:6]([CH3:77])[CH:5]=[CH:31][C:30]1=[O:32])[CH:34]=[CH2:35]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 57311555HCID 57311555, Verbindung

Produkt 1

HCID 5732367017-Allyl-12-[2-(4-tert-butyl-diphenylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2,3,10,16-tetraoneAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 14-acetoxy-17-allyl-12-[2-(4-tert-butyl-diphenylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (43.8 mg) in tetrahydrofuran (1.5 ml) was added potassium carbonate (ca 100 mg) at room temperature and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was diluted with diethyl ether and the resulting solution was washed with a saturated aqueous ammonium chloride, water and an aqueous sodium chloride successively, and dried over sodium sulfate. The resulting solution was concentrated under reduced pressure and the residue was purified on silica gel thin layer chromatography (developing solvent: diethyl ether and hexane, 3:2 v/v) to give 17-allyl-12-[2-(4-tert-butyl-diphenylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-14,18-diene-2,3,10,16-tetraone (30 mg).

Aufarbeitung

  1. washthe resulting solution was washed with a saturated aqueous ammonium chloride, water
  2. dry with materialan aqueous sodium chloride successively, and dried over sodium sulfate
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. customthe residue was purified on silica gel thin layer chromatography (developing solvent: diethyl ether and hexane, 3:2 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-a682ef506a49441faadb6b262178c18b
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06201005B1

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