Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(3'-cyano-4'-methylbiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216945

Reaktionsgleichung

Reaktionsgleichung von HRID 216945
[NH2:1][C:2](=O)[C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18]#[N:19])[CH:12]=2)=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:2]([C@@H:3]([NH:20][C:21]([C:23]1([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([C:18]#[N:19])[CH:12]=2)=[CH:7][CH:6]=1)#[N:1]

Komponenten

4

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568611(S)-tert-Butyl 4-(1-amino-3-(3'-cyano-4'-methylbiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Produkt 1

HCID 59568559(S)-tert-Butyl 4-(1-cyano-2-(3'-cyano-4'-methylbiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 4-(1-amino-3-(3′-cyano-4′-methylbiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 18, step (i), 154 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (145 mg) and the mixture was stirred at room temperature for 18 h. The solvent was partially evaporated and the mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1) to afford the sub-titled compound (127 mg).

Aufarbeitung

  1. customThe solvent was partially evaporated
  2. customthe mixture was purified by chromatography on silica eluting with ethyl acetate/isohexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-511794996dd44379ac3413d7181e3d40
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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