Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216968
[NH2:1][C:2](=O)[C@@H:3]([NH:23][C:24]([C:26]1([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[N:19]([CH3:20])[C:18](=[O:21])[CH2:17][S:16][C:15]=3[CH:22]=2)=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:2]([C@@H:3]([NH:23][C:24]([C:26]1([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[N:19]([CH3:20])[C:18](=[O:21])[CH2:17][S:16][C:15]=3[CH:22]=2)=[CH:7][CH:6]=1)#[N:1]

Komponenten

4

Edukt 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568625(S)-tert-Butyl 4-(1-amino-3-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Produkt 1

HCID 59568616(S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 4-(1-amino-3-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 28, step (ii), 138 mg) in dichloromethane (10 mL) was treated with Burgess' reagent (116 mg) and stirred at room temperature for 18 h. The solvent was partially evaporated and the residue absorbed onto silica and purified by chromatography on silica eluting with ethyl acetate/isohexane (50:50 to 70:30) to afford the sub-titled compound (120 mg).

Aufarbeitung

  1. customThe solvent was partially evaporated
  2. customthe residue absorbed onto silica
  3. custompurified by chromatography on silica eluting with ethyl acetate/isohexane (50:50 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-c8f0055a97074f7dadfe405badef11df
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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