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

HRID 17089

Reaktionsgleichung

Reaktionsgleichung von HRID 17089
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=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:31])[CH3:30])[CH:26]=[CH:25][C:24]=1[O:32][CH3:33])[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>[C:29]([C:27]1[CH:26]=[CH:25][C:24]([O:32][CH3:33])=[C:23]([C:14]2[CH:15]=[CH:16][C:17]([C:19]([F:21])([F:22])[F:20])=[CH:18][C:13]=2[CH2:12][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:41])[F:42])[CH:36]=[C:35]([C:37]([F:38])([F:40])[F:39])[CH:34]=2)[C:8](=[O:11])[O:9][CH3:10])[CH:28]=1)(=[O:31])[CH3:30]

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 11599738Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(1-hydroxyethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Produkt 1

HCID 11563435Methyl {[5'-acetyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3,5-bis(trifluoromethyl)benzyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl [3,5-bis(trifluoromethyl)benzyl]{[5′-(1-hydroxyethyl)-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 140, 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 2:3 EtOAc:hexane. 1H NMR (CDCl3, 600 MHz) δ 8.02 (d, J=7.8 Hz, 1H), 7.76 (d, J=2.4 Hz, 1H), 7.73 (s, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.32-7.55 (m, 4H), 6.99 (m, 1H),4.18-4.58 (m, 4H), 3.79 (s, 3H), 3.69-3.76 (m, 3H), 2.57 (s, 3H). LC-MS (M+1) 608.3 (4.19 min).

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-eb68d474425c40a49198bd7c7f5a63ea
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737295B2

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