Diisopropylethylamine → 3,3,3-Trifluoro-propane-1-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide

HRID 1783410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783410
C(OC(=O)[NH:7][C@@H:8]1[CH2:14][C:13]([F:16])([F:15])[CH2:12][CH2:11][N:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])[C:9]1=[O:28])(C)(C)C.Cl.O1CCOCC1.CCN(C(C)C)C(C)C.[F:46][C:47]([F:55])([F:54])[CH2:48][CH2:49][S:50](Cl)(=[O:52])=[O:51]>ClCCl>[CH3:27][O:26][C:19]1[CH:20]=[C:21]([O:24][CH3:25])[CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[CH2:11][CH2:12][C:13]([F:15])([F:16])[CH2:14][C@@H:8]([NH:7][S:50]([CH2:49][CH2:48][C:47]([F:55])([F:54])[F:46])(=[O:52])=[O:51])[C:9]1=[O:28]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27611773,3,3-Trifluoropropane-1-sulfonyl chlorideHCID 204431481,4-Dioxane hydrochlorideHCID 57589908[(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 866107413,3,3-Trifluoro-propane-1-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

[(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.85 g, 1.85 mmol) was dissolved in 38 ml dichloromethane. 4 M HCl/1,4-dioxan (20 ml) were added dropwise and the mixture was allowed to react for 1 h. The reaction mixture was concentrated under reduced pressure and concentrated once from acetonitrile. To 291 mg of the resultant hydrochloride salt was added CH2Cl2 (20 ml) followed by the dropwise addition of Hünig's base (0.36 ml, 2.1 mmol). A solution of 3,3,3-trifluoropropane-1-sulfonyl chloride (0.19 g, 0.9 mmol) in CH2Cl2 (5 ml) was added and the reaction mixture (pH 8) was stirred for a further 1.5 h. The reaction mixture was purified over silica gel (heptane-ethylacetate, 95:5-0:100): white solid 0.30 g (77%);

Aufarbeitung

  1. customto react for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. concentrationconcentrated once from acetonitrile
  4. additionTo 291 mg of the resultant hydrochloride salt was added CH2Cl2 (20 ml)
  5. customThe reaction mixture was purified over silica gel (heptane-ethylacetate, 95:5-0:100)

Quellen und Nachweise

ORD-Eintrag
ord-fdb5fc0982a645b89c3170eee4de6216
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501406B2

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