Diisopropylethylamine → (2S,3R)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanamido)-3-hydroxy-3-(4-methoxyphenyl)propanoate

HRID 58809

Reaktionsgleichung

Reaktionsgleichung von HRID 58809
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:34][C@@H:35]([C@H:46]([OH:55])[C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=1)[C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37].[NH:56]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[C@H:57]([C:60](O)=[O:61])[CH2:58][OH:59]>CN(C=O)C>[C:66]([O:65][C:63]([NH:56][C@@H:57]([CH2:60][OH:61])[C:58]([NH:34][C@@H:35]([C@H:46]([OH:55])[C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=1)[C:36]([O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:37])=[O:59])=[O:64])([CH3:69])([CH3:68])[CH3:67]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117607803(2S,3R)-benzyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate

Produkt 1

HCID 131737019(2S,3R)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanamido)-3-hydroxy-3-(4-methoxyphenyl)propanoateAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sequentially HATU (645 mg, 1.70 mmol) and DIEA (0.99 mL, 5.7 mmol) were added to a 0° C. solution of (2S,3R)-benzyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate (HCl salt, 477 mg, 1.41 mmol) and Boc-Ser-OH (290 mg, 1.41 mmol) in DMF (8 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 30 min. The mixture was concentrated and the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=2:1) twice to afford (2S,3R)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanamido)-3-hydroxy-3-(4-methoxyphenyl)propanoate (646 mg, 93% yield) as a colorless solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=2:1) twice

Quellen und Nachweise

ORD-Eintrag
ord-514e7be395af4c72920394a73b5673db
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434761B2

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