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Diisopropylethylamine → HCID 71197908, Verbindung

HRID 2415542
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2415542
C(N(CC)C(C)C)(C)C.Cl.[C:11]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C@H:17](C(O)=O)[CH2:16]1)([CH3:14])([CH3:13])[CH3:12].Cl.[Cl:32][C:33]1[CH:34]=[CH:35][C:36]([C:44]2[CH2:45][CH2:46][NH:47][CH2:48][CH:49]=2)=[C:37]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:38]=1.F[P-](F)(F)(F)(F)F.N1([O:66][C:67](N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.ON1C2N=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:11]([N:15]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=2[F:27])[C@H:17]([C:67]([N:47]2[CH2:46][CH:45]=[C:44]([C:36]3[CH:35]=[CH:34][C:33]([Cl:32])=[CH:38][C:37]=3[CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH2:49][CH2:48]2)=[O:66])[CH2:16]1)([CH3:12])([CH3:14])[CH3:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67212109(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid hydrochloride
HCID 86590371
HCID 86590371, Verbindung

Produkt 1

HCID 71197908HCID 71197908, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N-diisopropylethylamine (1.36 mL, 7.80 mmol) was added to a stirred suspension of (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid (1-7) (0.831 g, 2.60 mmol), methyl [5-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]acetate hydrochloride (1-6) (0.690 g, 2.60 mmol), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.19 g, 3.12 mmol) and 1-hydroxy-7-azabenzotriazole (0.425 g, 3.12 mmol) in N,N-dimethylformamide (5.2 mL) at ambient temperature. After approximately 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate. The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-15% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent) provided 1-8 as a pale yellow oil (m/z (ES) 531 (MH+).

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-15% methanol (containing 10% v/v ammonium hydroxide)/methylene chloride as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-d907e828abaa47ddb437d0fe469e85ac
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06818658B2

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