TfOH-TFA → 5-Chloro-thiophene-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-(6-methoxy-pyridin-3-ylmethyl)-amide

HRID 1783415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783415
FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.COC1C=C(OC)C=CC=1C[N:21]1[CH2:27][CH2:26][C:25]([F:29])([F:28])[CH2:24][C@@H:23]([N:30]([CH2:40][C:41]2[CH:42]=[N:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[S:31]([C:34]2[S:35][C:36]([Cl:39])=[CH:37][CH:38]=2)(=[O:33])=[O:32])[C:22]1=[O:49]>ClCCl>[F:29][C:25]1([F:28])[CH2:26][CH2:27][NH:21][C:22](=[O:49])[C@H:23]([N:30]([CH2:40][C:41]2[CH:42]=[N:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[S:31]([C:34]2[S:35][C:36]([Cl:39])=[CH:37][CH:38]=2)(=[O:33])=[O:32])[CH2:24]1

Komponenten

4

Edukt 2

HCID 18539426TfOH-TFAHCID 866107445-Chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide

Produkt 1

HCID 444556095-Chloro-thiophene-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-(6-methoxy-pyridin-3-ylmethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture containing trifluoroacetic acid/trifluoromethanesulfonic acid (5:2 v/v, 0.62 ml) was added to 5-chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide (0.17 g, 0.19 mmol) in dichloromethane (10 ml). After 2 h the reaction mixture was concentrated under reduced pressure and the residue taken up in ethyl acetate and washed with water, saturated aqueous sodium bicarbonate and brine, dried (Na2SO4), filtered, concentrated under reduced pressure and purified over silica gel (heptane-ethylacetate, 9:1-0:1): white solid 69 mg (77%);

Aufarbeitung

  1. concentrationAfter 2 h the reaction mixture was concentrated under reduced pressure
  2. washwashed with water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified over silica gel (heptane-ethylacetate, 9:1-0:1)

Quellen und Nachweise

ORD-Eintrag
ord-062a2d5b66be42e89939bac9741e1198
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501406B2

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