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Diisopropylethylamine → HCID 86726297, Verbindung

HRID 1422880
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1422880
[NH2:1][C@H:2]([C:12](=[O:20])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9](=[O:11])[CH3:10].FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[O:70]=[C:71]1[C@H:75]([C:76](O)=[O:77])[C@@H:74]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:73][NH:72]1>C(Cl)Cl.CN(C=O)C>[O:70]=[C:71]1[CH:75]([C:76]([NH:1][C@H:2]([C:12](=[O:20])[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9](=[O:11])[CH3:10])=[O:77])[CH:74]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:73][NH:72]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 762604HCID 762604, VerbindungHCID 2724699PyBOPHCID 86726298HCID 86726298, Verbindung

Produkt 1

HCID 86726297HCID 86726297, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22350042
dichloromethane N,N-dimethylformamide
Lösungsmittel

Versuchsvorschrift

Thioacetic acid S—((S)-6-amino-6-phenylcarbamoyl-hexyl) ester-trifluoroacetate (1.03 mmol), DIPEA (3.08 mmol) and PyBOP (1.03 mmol) were added to a solution of (3R*,4S*)-2-oxo-4-phenyl-pyrrolidine-3-carboxylic acid in DCM/DMF: 5/9. The resulting reaction mixture was stirred at RT overnight. After removal of the solvent under reduced pressure, the resulting solid was poured into water and extracted twice with AcOEt. The organic layer was then washed with NaHCO3, water and brine before being dried over Na2SO4 and concentrated under reduced pressure to yield an oil. The latter was partially purified by silica gel chromatography and then subjected to HPLC purification.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter removal of the solvent under reduced pressure
  3. additionthe resulting solid was poured into water
  4. extractionextracted twice with AcOEt
  5. washThe organic layer was then washed with NaHCO3, water and brine
  6. dry with materialbefore being dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto yield an oil
  9. customThe latter was partially purified by silica gel chromatography
  10. customsubjected to HPLC purification

Quellen und Nachweise

ORD-Eintrag
ord-7fe0b12d0a7346b9ae8286c1b01efb0e
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08927533B2

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