Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(2-(4'-(azetidin-1-ylsulfonyl)biphenyl-4-yl)-1-cyanoethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216921
[NH2:1][C:2](=O)[C@@H:3]([NH:24][C:25]([C:27]1([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:23][CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[N:20]1([S:17]([C:14]2[CH:13]=[CH:12][C:11]([C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C@H:3]([NH:24][C:25]([C:27]4([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[O:26])[C:2]#[N:1])=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)(=[O:19])=[O:18])[CH2:23][CH2:22][CH2:21]1

Komponenten

4

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 70213622(S)-tert-Butyl 4-(1-amino-3-(4'-(azetidin-1-ylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Produkt 1

HCID 70211210(S)-tert-Butyl 4-(2-(4'-(azetidin-1-ylsulfonyl)biphenyl-4-yl)-1-cyanoethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 4-(1-amino-3-(4′-(azetidin-1-ylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 7, step (i), 309 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (251 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and then purified by chromatography on silica using diethyl ether and then 1:1 ethyl acetate/isohexane as eluent to yield a white solid (222 mg).

Aufarbeitung

  1. customThe solvent was partially evaporated
  2. custompurified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-f0efc4c3558c48e1916dd659f8116b81
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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