Trifluoroacetic acid → tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino)-3-oxopropyl]pyrrolidine-1-carboxylate

HRID 1022523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022523
C(O[C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)=[O:10])(C)(C)C.[C:25]([O:29][C:30]([NH:32][C@@:33]1(C(O)=O)[CH2:35][C@@H:34]1[C:36]1[CH:41]=[CH:40][CH:39]=CC=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].FC(F)(F)[C:47](O)=[O:48].[CH2:52](OC(N[C@H](C(N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(OC(C)(C)C)=O)=O)C(C)C)=O)C1C=CC=CC=1>>[CH3:47][O:48][C@@H:41]([C@@H:36]1[CH2:34][CH2:35][CH2:33][N:32]1[C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[C@@H:40]([CH3:39])[C:6]([NH:7][C@@:8]1([C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[O:10])[CH2:52][C@@H:17]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:24]

Komponenten

5

Edukt 4

HCID 6422Trifluoroacetic acidHCID 7009512(1S,2R)-N-Boc-1-amino-2-phenylcyclopropanecarboxylic acidHCID 10529182(3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoateHCID 89181604tert-Butyl[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate3×

Produkt 1

HCID 86678340tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(1S,2R)-1-(1,2-oxazinan-2-ylcarbonyl)-2-phenylcyclopropyl]amino)-3-oxopropyl]pyrrolidine-1-carboxylate

Versuchsvorschrift

The title compound was prepared analogously to the synthesis of Intermediates 5 and 6 in three steps by coupling commercially available (1S,2R)-1-[(tert-butoxycarbonyl)amino]-2-phenylcyclopropanecarboxylic acid with 1,2-oxazinane hydrochloride (Starting Material 5), subsequent deprotection with trifluoroacetic acid and another coupling with Starting Material 1. The end product was purified by preparative HPLC.

Aufarbeitung

  1. customThe end product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d526ba0a9af74003bc4599b3c4675786
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722629B2

Notizen zur Reaktion

Wird geladen…