Methanesulfonyl chloride → HCID 86603641, Verbindung

HRID 226329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226329
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10]O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.CS(Cl)(=O)=O.Cl.Cl.[C:19]([O:23][C:24]([N:26]([C@@H:40]1[CH2:44][CH2:43][NH:42][CH2:41]1)[C:27]1[N:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CCN(CC)CC.C1COCC1>[C:19]([O:23][C:24]([N:26]([C@@H:40]1[CH2:44][CH2:43][N:42]([CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][CH2:3][C:4]=3[CH:9]=2)[CH2:41]1)[C:27]1[N:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:29][CH:28]=1)=[O:25])([CH3:20])([CH3:21])[CH3:22]

Komponenten

6

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanolHCID 86603639ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride

Produkt 1

HCID 86603641HCID 86603641, VerbindungAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

To a mixture of 2,3-dihydro-1-benzofuran-5-ylmethanol (95.1 mg), Et3N (0.120 mL), and THF (3 mL) was added methanesulfonyl chloride (0.053 mL) at 4° C. The reaction mixture was stirred for 3 hours, and added ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride (250 mg) and Et3N (0.281 mL). After stirring for 2 hours at 60° C., the resulting mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2,3-dihydro-1-benzofuran-5-ylmethyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate (134 mg).

Aufarbeitung

  1. stirringAfter stirring for 2 hours at 60° C.
  2. customthe resulting mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-921a89893f8a4239a874a3f306929314
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557127B2

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