Diisopropylethylamine → HCID 66899848, Verbindung

HRID 19043

Reaktionsgleichung

Reaktionsgleichung von HRID 19043
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C@@H:14]([O:16][CH2:17][CH3:18])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH:20][C@@H:21]([CH2:51]O)[CH2:22][N:23]1[CH:27]=[CH:26][C:25]([NH:28]C(=O)[C@@H](N2CC(OC3C=CC=C(Cl)C=3Cl)=CC2=O)CC(C)C)=[N:24]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:63]=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH:28][C:25]1[CH:26]=[CH:27][N:23]([CH2:22][C:21]([OH:20])([CH3:51])[CH3:63])[N:24]=1)[CH2:13][C@@H:14]([O:16][CH2:17][CH3:18])[CH3:15])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66899094HMS5552 HClHCID 86635230(2S,4S)-2-t-butoxycarbonylamino-4-ethoxy-pentanoic acid

Produkt 1

HCID 66899848HCID 66899848, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(2S,4S)-2-t-butoxycarbonylamino-4-ethoxy-pentanoic acid (401 mg, 1.536 mmol) was mixed with 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (prepared in U.S. Pat. Appl. US2008021032 Example 80, 334 mg, 2.16 mmol) in N,N-dimethylformamide (10 mL). benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (1.23 g, 2.77 mmol) and N,N-diisopropylethylamine (0.7 mL) was added at 0° C. The mixture was stirred at room temperature overnight. Solvents were evaporated and the residue was extracted with ethyl acetate and saturated sodium chloride solution. The solvents were evaporated and the crude material was purified by flash column chromatography (silica gel, 10-80% ethyl acetate/hexanes) to afford {(1S,3S)-3-ethoxy-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-butyl}-carbamic acid t-butyl ester (486 mg, 80%) as a white solid: LR-ES-MS m/z calculated for C19H34N4O5 [M]+ 398, observed [M+H]+ 399.

Aufarbeitung

  1. customSolvents were evaporated
  2. extractionthe residue was extracted with ethyl acetate and saturated sodium chloride solution
  3. customThe solvents were evaporated
  4. customthe crude material was purified by flash column chromatography (silica gel, 10-80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-57aa69201bd24472ae91f3b3dcdc10d7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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