Diisopropylethylamine → (S)-6-Hydroxy-2-{(S)-2-[(S)-3-(4-hydroxy-phenyl)-2-methyl-propionylamino]-4-methyl-pentanoylamino}-hexanoic acid methyl ester

HRID 2371338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371338
C(OC(N[C@@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[C:13]([NH:15][C@@H:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]([OH:19])=O)=[O:14])=O)C1C=CC=CC=1.[CH3:32][O:33][C:34](=[O:42])[C@@H:35]([NH2:41])[CH2:36][CH2:37][CH2:38][CH2:39][OH:40].[CH3:43]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:32][O:33][C:34](=[O:42])[C@@H:35]([NH:41][C:17](=[O:19])[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([CH3:43])[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=1)[CH2:20][CH:21]([CH3:22])[CH3:23])[CH2:36][CH2:37][CH2:38][CH2:39][OH:40]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11680006AG-H-13503HCID 44191152Z-Tyr-Leu-OH

Produkt 1

HCID 66847133(S)-6-Hydroxy-2-{(S)-2-[(S)-3-(4-hydroxy-phenyl)-2-methyl-propionylamino]-4-methyl-pentanoylamino}-hexanoic acid methyl esterAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of (S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionyl-amino]-4-methyl pentanoic acid (Bachem) (5.44 mmol, 1.36 g, 1 eq) and methyl ester 82 (5.44 mmol, 0.91 g) in DMF was added HATU (5.98 mmol, 1.41 g, 1.1 eq). DIPEA (0.12 mol, 1.62 g, 2.1 eq) was added and the reaction mixture was stirred at room temperature overnight. EtOAc (100 mL) was added the mixture was washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by recrystallisation from EtOAc to provide diol 83 as an oil (2.39 g, 76%).

Aufarbeitung

  1. washwas washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by recrystallisation from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-9df7d80dd18c411488fbc97ce5a32c09
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710178B2

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