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Diisopropylethylamine → HCID 86714380, Verbindung

HRID 1750169
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1750169
[NH2:1][C@@H:2]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][OH:4].CCN(C(C)C)C(C)C.[CH:21]1([CH2:26][C:27]2[N:31]([CH:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[C:30]3[CH:37]=[CH:38][C:39]([C:41](Cl)=[O:42])=[CH:40][C:29]=3[N:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1>C1COCC1>[CH:6]1([CH2:5][C@H:2]([NH:1][C:41]([C:39]2[CH:38]=[CH:37][C:30]3[N:31]([CH:32]([CH2:33][CH3:34])[CH2:35][CH3:36])[C:27]([CH2:26][CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:28][C:29]=3[CH:40]=2)=[O:42])[CH2:3][OH:4])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 444569(2S)-2-amino-3-cyclohexylpropan-1-olHCID 867143812-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carbonyl chloride

Produkt 1

HCID 86714380HCID 86714380, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

47 mg of (S)-2-amino-3-cyclohexyl-propan-1-ol and 0.14 ml DIPEA were dissolved in 2 ml dry THF. The mixture was cooled to −10° C. and 67 mg of 2-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carbonyl chloride in 1 ml of dry THF were added. The mixture was stirred under exclusion of moisture for 15 min at −10° C. and then at RT over night. It was then filtered, the filter was washed with 10 ml ethyl acetate. The filtrate was evaporated, the residue was taken up in 20 ml ethyl acetate and extracted with 20 ml 5% NaHCO3. The organic phase was dried and evaporated and the residue was purified by HPLC to yield 24 mg (27%) of 2-cyclopentylmethyl-1-(1-ethyl-propyl)-1H-benzoimidazole-5-carboxylic acid ((S)-1-cyclohexylmethyl-2-hydroxy-ethyl)-amide.

Aufarbeitung

  1. waitat RT over night
  2. filtrationIt was then filtered
  3. washthe filter was washed with 10 ml ethyl acetate
  4. customThe filtrate was evaporated
  5. extractionextracted with 20 ml 5% NaHCO3
  6. customThe organic phase was dried
  7. customevaporated
  8. customthe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5747ad06e7134889b0ba33e00e1b63cf
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09156796B2

Notizen zur Reaktion

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