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

Diisopropylethylamine → (S)-2-{4-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide

HRID 19376
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 19376
[OH:1][C:2]([CH3:26])([CH3:25])[CH2:3][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][C:8]1[CH2:12][N:11]([C@@H:13]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:14]([OH:16])=O)[C:10](=[O:21])[CH:9]=1.Cl.[OH:28][C@@H:29]([CH2:59]O)[CH2:30][N:31]1[CH:35]=[CH:34][C:33]([NH:36]C(=O)[C@@H](N2CC(OC3C=CC=C(Cl)C=3Cl)=CC2=O)CC(C)C)=[N:32]1.[CH:61](N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[OH:28][C:29]([CH3:59])([CH3:61])[CH2:30][N:31]1[CH:35]=[CH:34][C:33]([NH:36][C:14](=[O:16])[C@@H:13]([N:11]2[CH2:12][C:8]([O:7][C:6]3[CH:22]=[CH:23][CH:24]=[C:4]([CH2:3][C:2]([OH:1])([CH3:26])[CH3:25])[CH:5]=3)=[CH:9][C:10]2=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19])=[N:32]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66895240HCID 66895240, VerbindungHCID 66899094HMS5552 HCl

Produkt 1

HCID 57920169(S)-2-{4-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide
Ausbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-{4-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid (prepared as in Example 235, 0.159 g, 0.44 mmol) in N,N-dimethylformamide (5 mL) was added 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (prepared in U.S. Pat. Appl. US2008021032 Example 80, 0.102 g, 0.66 mmol), N,N-diisopropylethylamine (0.312 g, 2.41 mmol) and benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.778 g, 1.76 mmol) at 0° C. The mixture was allowed to slowly warm up to room temperature and stirred for 48 h. The mixture was then concentrated in vacuo, the residue taken up in ethyl acetate and washed with aqueous saturated ammonium chloride and brine and then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by ISCO column chromatography (Silicycle 40 g, 10% to 100% ethyl acetate/hexanes) which afforded (S)-2-{4-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid [1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-amide (0.060 g, 30%) as a white solid: HR-ES-MS m/z calculated for C27H38N4O5 [M+H]+ 499.2915, observed 499.2915; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.83-0.97 (m, 6H), 1.06 (br. s., 12H), 1.36-1.63 (m, 2H), 1.66-1.86 (m, 1H), 2.68 (s, 2H), 3.89 (s, 2H), 4.18 (d, J=18.1 Hz, 1H), 4.37 (d, J=1.8 Hz, 1H), 4.57 (d, J=18.1 Hz, 1H), 4.68 (d, J=1.5 Hz, 1H), 4.83 (s, 1H), 4.84-4.94 (m, 1H), 6.44 (s, 1H), 7.07-7.19 (m, 3H), 7.27-7.42 (m, 1H), 7.54 (s, 1H), 10.78 (s, 1H).

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed with aqueous saturated ammonium chloride and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by ISCO column chromatography (Silicycle 40 g, 10% to 100% ethyl acetate/hexanes) which

Quellen und Nachweise

ORD-Eintrag
ord-ffd37df479c14c65923be94202df6ca8
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741327B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion