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Triacetoxyperiodinane → Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-(trifluoroacetyl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 17090
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17090
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]([OH:34])[C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:24]=1[O:35][CH3:36])[C:8](=[O:11])[O:9][CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)C>[F:1][C:2]([F:44])([F:45])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([C:29](=[O:34])[C:30]([F:31])([F:32])[F:33])[CH:26]=[CH:25][C:24]=1[O:35][CH3:36])[C:8](=[O:11])[O:9][CH3:10]
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Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 11542018Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-(2,2,2-trifluoro-1-hydroxyethyl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Produkt 1

HCID 86615400Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-(trifluoroacetyl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl Ether
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl [3,5-bis(trifluoromethyl)benzyl]{[2′-methoxy-5′-(2,2,2-trifluoro-1-hydroxyethyl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 139, 29 mg, 0.048 mmol) was dissolved in methylene chloride, and Dess-Martin periodinane (31 mg, 0.072 mmol) was added. Once the reaction was complete, the solution was diluted in diethyl ether and washed sequentially with saturated sodium thiosulfate, saturated sodium bicarbonate and water. The aqueous extracts were combined and back extracted with diethyl ether, then recombined with the previous organic layers. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained by preparative thin layer chromatography using 1:3 acetone:hexane.

Aufarbeitung

  1. washwashed sequentially with saturated sodium thiosulfate, saturated sodium bicarbonate and water
  2. extractionback extracted with diethyl ether
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9d59393c4c9049a0808495226bbc11b0
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737295B2

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