Methyl N-(triethylammoniosulfonyl)carbamate → (S)-4'-(2-(4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-2-cyanoethyl)biphenyl-4-yl methanesulfonate

HRID 216919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216919
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([NH:23][C:24]([C:26]3([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[C:20]([NH2:22])=O)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][C@H:19]([NH:23][C:24]([C:26]3([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[C:20]#[N:22])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Komponenten

4

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568621(S)-4'-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-4-yl methanesulfonate

Produkt 1

HCID 59568586(S)-4'-(2-(4-(tert-Butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-2-cyanoethyl)biphenyl-4-yl methanesulfonateAusbeute 117,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-4′-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-4-yl methanesulfonate (Example 6, step (i), 234 mg) in dichloromethane (8 mL) was treated with Burgess' reagent (199 mg) and the mixture was stirred at room temperature for 18 h. It was partially evaporated and then purified by chromatography on silica using diethyl ether and then 1:1 ethyl acetate/isohexane as eluent to a afford the sub-titled compound as a white solid (267 mg).

Aufarbeitung

  1. customIt was partially evaporated
  2. custompurified by chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-d41edf7901e84abf88064f54e6492c69
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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