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Acetic Acid → 7-{2-[(4-Cyano-benzenesulfonyl)-methyl-amino]-ethyl}-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 1992354
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1992354
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH3:16])[CH2:13][CH:14]=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[C:17]([O:21][C:22]([N:24]1[CH2:31][CH:30]2[O:32][CH:26]([CH2:27][NH:28][CH2:29]2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C.[BH3-]C#N.[Na+]>ClCCl>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH:26]2[O:32][CH:30]([CH2:29][N:28]([CH2:14][CH2:13][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH3:16])[CH2:27]2)[CH2:31]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 866259934-Cyano-N-methyl-N-(2-oxo-ethyl)-benzenesulfonamide2×

Produkt 1

HCID 685191317-{2-[(4-Cyano-benzenesulfonyl)-methyl-amino]-ethyl}-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of step (ii) product 4-Cyano-N-methyl-N-(2-oxo-ethyl)-benzenesulfonamide (4.97 g), and 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (4.95 g; see WO 01/28992) and acetic acid (1.7 ml) in dry dichloromethane (50 ml) was stirred at RT for 3 h and then cooled to 0° C. NaBH3CN (1.96 g, 0.0312 mol) was added and stirring continued at RT overnight under nitrogen atmosphere. The reaction mixture was quenched with water, extracted with dichloromethane, washed with water and brine and dried over sodium sulfate. Solvent evaporated under reduced pressure and the residue was purified by column chromatography over silica gel using 28% ethyl acetate in petroleum ether eluent to give the sub-title compound (2.2 g) as a liquid.

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporated under reduced pressure
  6. customthe residue was purified by column chromatography over silica gel using 28% ethyl acetate in petroleum ether eluent

Quellen und Nachweise

ORD-Eintrag
ord-87cf067e08ae4f2abec07e760bf521be
Quelldatensatz
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07648985B2

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