5-Chlorothiophene-2-sulfonyl chloride → HCID 58748187, Verbindung

HRID 1162615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162615
Cl.Cl.[CH2:3]([O:5][C:6](=[O:14])[CH2:7][N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)[CH3:4].[Cl:15][C:16]1[S:20][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:18][CH:17]=1>C1COCC1.CCOC(C)=O>[CH2:3]([O:5][C:6](=[O:14])[CH2:7][N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][S:21]([C:19]2[S:20][C:16]([Cl:15])=[CH:17][CH:18]=2)(=[O:23])=[O:22])[CH2:9]1)[CH3:4]

Komponenten

5

Edukt 2

HCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 68646554HCID 68646554, Verbindung

Produkt 1

HCID 58748187HCID 58748187, VerbindungAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

8.1 A suspension of 540 mg ((R)-3-amino-pyrrolidin-1-yl)-acetic acid ethyl ester dihydrochloride (example 1.2) in 5 ml THF was treated with 1.2 ml TEA and 530 mg 5-chlorothiophene-2-sulfonylchloride. The reaction mixture was stirred over night at r.t., then taken up in EtOAc and washed with water and brine. The organic layer was dried over MgSO4, filtered and concentrated to give 690 mg [(R)-3-(5-chloro-thiophene-2-sulfonylamino)-pyrrolidin-1-yl]-acetic acid ethyl ester. Oil. 353.1 ([M+H]+)

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cd4cf1d2b8bf4cc6b215522d5a23cc5b
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820699B2

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