Benzyl chloroformate → [4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl ester

HRID 337202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337202
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>C1COCC1.C(Cl)Cl>[CH2:35]([O:34][C:32](=[O:33])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 71618273N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide

Produkt 1

HCID 71449433[4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl esterAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide (0.09 g, 0.3 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.1 ml, 0.6 mmol) in one portion followed by the drop wise addition of benzyl chloroformate (0.05 ml, 0.33 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 100% EtOAc) to give the title compound (0.04 g, 34% yield) as a white powder.

Aufarbeitung

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (elution: 100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c8d40014bebf4708ad8cc61cd3084959
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889716B2

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