StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisopropylethylamine → (3RS)-3-{5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid ethyl ester

HRID 49700
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49700
F[C:2](F)(F)[C:3](O)=O.[C:8]1([CH3:40])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1N[C:17]2[CH:23]=[C:22]([CH2:24][C:25]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([CH:34]([CH3:39])[CH2:35][C:36]([OH:38])=[O:37])=[N:32][CH:33]=3)=[O:26])[CH:21]=[CH:20][C:18]=2[N:19]=1.F[P-](F)(F)(F)(F)F.N1([O:57]C(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.NC1C=CC(C(C)CC(OCC)=O)=NC=1>CN(C)C=O>[CH2:2]([O:38][C:36](=[O:37])[CH2:35][CH:34]([C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:25](=[O:26])[CH2:24][C:22]2[CH:21]=[CH:20][C:18]3[N:19]=[C:15]([NH:14][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[CH3:40])[O:57][C:17]=3[CH:23]=2)=[CH:33][N:32]=1)[CH3:39])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9829176(3RS)-3-{5-[2-(2-o-Tolylamino-3H-benzimidazol-5-yl)-acetylamino]-pyridin-2-yl}-butyric acid trifluoroacetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17946645ethyl (3RS)-3-(5-aminopyrid-2-yl)butyrate

Produkt 1

HCID 9890975
(3RS)-3-{5-[2-(2-o-tolylamino-benzoxazol-6-yl)-acetylamino]-pyrid-2-yl}-butyric acid ethyl ester
Ausbeute 140,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A stirred solution of 2-o-tolylamino-benzoxazol-6-acetic acid (0.42 g, Reference Example 2) in dimethylformamide (15 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.57 g), then with diisopropylethylamine (0.4 g) and then with a solution of ethyl (3RS)-3-(5-aminopyrid-2-yl)butyrate (0.3 g, Reference Example 5) in dimethylformamide (5 mL). The mixture was stirred at room temperature for 5 hours then left to stand over night and then evaporated to low bulk. The residue was partitioned between water and ethyl acetate. The organic phase was washed with dilute acetic acid, then with water, then with aqueous bicarbonate solution (5%), then with water, then with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate to give the title compound (0.5 g) as a colourless glass. TLC: RF=0.36 (eluting with ethyl acetate). MS: 473 (MH+).

Aufarbeitung

  1. waitthen left
  2. waitto stand over night
  3. customevaporated to low bulk
  4. customThe residue was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with dilute acetic acid
  6. dry with materialwith water, then with aqueous bicarbonate solution (5%), then with water, then with brine, then dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ab39d4a2592841388c2555f65dd8ac8e
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06706738B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion