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Ammonia → 4-(5-Hydroxymethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1352369
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1352369
OO.[OH-].[Na+].[CH:5]([CH:7]=[CH2:8])=[O:6].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH:17]1C(=S)N)=[O:15])([CH3:12])([CH3:11])[CH3:10].N1(C(OC(C)(C)C)=O)CCNCC1.[C:38](N1C=CN=C1)([N:40]1C=CN=C1)=[S:39].N>O.C(OCC)(=O)C.O1CCCC1.C(O)C>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][N:19]([C:38]2[S:39][C:7]([CH2:5][OH:6])=[CH:8][N:40]=2)[CH2:20][CH2:21]1)=[O:15])([CH3:10])([CH3:11])[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 7

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 7847AcroleinHCID 14798Sodium Hydroxide2×HCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86606773
Thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 675498134-(5-Hydroxymethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 21939870Tetrahydrofuran ethyl acetateLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of 179 mmol 30% aqueous hydrogen peroxide in 60 ml water was added 1 N aqueous sodium hydroxide solution until the pH was 9. The reaction mixture was then cooled to 10° C. and 163 mmol acrolein was added dropwise. Further amounts of 1 N aqueous sodium hydroxide solution were added during the addition in order to maintain the pH of the reaction mixture between pH 8 and 9. The mixture was stirred for 30 min at 0° C. and then 40.8 mmol thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (prepared from tert-butyl 1-piperazinecarboxylate, 1,1′-thiocarbonyldiimidazole and ammonia according to the procedure of J. Med. Chem. 1998, 41, 5037–5054) was added. To the resulting suspension was added 25 ml ethanol and the mixture was heated at 80° C. for 30 min. The resulting solution was diluted with ethyl acetate/tetrahydrofuran (1:1) and the mixture was washed twice with brine. The organic phase was dried over sodium sulphate and concentrated in vacuo to afford the title compound as a yellow oil (yield 99%). MS (m/e): 300.3 (M+H+, 100%).

Aufarbeitung

  1. temperatureto maintain the pH of the reaction mixture between pH 8 and 9
  2. addition1998, 41, 5037–5054) was added
  3. temperaturethe mixture was heated at 80° C. for 30 min
  4. washthe mixture was washed twice with brine
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5567423f99f3431fa0cb7f13c3cc56fb
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07220744B2

Notizen zur Reaktion

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