Triethylamine → Methanesulfonic acid [(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)-phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methyl ester

HRID 747003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747003
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:38])([F:37])[C:8]1[CH:9]=[C:10]([C@H:18]([O:20][C@@H:21]2[C@@H:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[C@H:25]([CH2:35][OH:36])[CH2:24][CH2:23][O:22]2)[CH3:19])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1.C(N(CC)CC)C>ClCCl>[F:38][C:7]([F:6])([F:37])[C:8]1[CH:9]=[C:10]([C@H:18]([O:20][C@@H:21]2[C@@H:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[C@H:25]([CH2:35][O:36][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:24][CH2:23][O:22]2)[CH3:19])[CH:11]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11420320[(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methanol

Produkt 1

HCID 86606915Methanesulfonic acid [(2R,3R,4R)-2-[(1R)-1-(3,5-Bis(trifluoromethyl)-phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (50 μl, 0.63 mmol) was added to a mixture of [(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(3,4-difluorophenyl)-tetrahydropyran-4-yl]methanol (Description 15; 235 mg, 0.49 mmol), triethylamine (133 ml, 0.97 mmol), 4-N,N-dimethylaminopyridine (3 mg, 0.02 mmol) and dichloromethane (5 ml) at 0° C. The mixture was stirred for 30 minutes, then quenched with saturated aqueous NaHCO3 and extracted into dichloromethane. The combined organic extracts were dried and concentrated. The product was used in the next step without further purification.

Aufarbeitung

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted into dichloromethane
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe product was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-e9a5425ad2fe4bf098f8a3fec1ebc7cb
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07393858B2

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