Trifluoroacetic acid → tert-Butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3,3-diphenylpropan-2-yl]amino}-3-oxopropyl]pyrrolidine-1-carboxylate

HRID 1022521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022521
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@H:33](C(O)=O)[CH:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43]C=1)C1C=CC=CC=1)=[O:31])([CH3:28])([CH3:27])[CH3:26].FC(F)(F)[C:52](O)=[O:53].C(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)[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>>[CH3:52][O:53][C@@H:45]([C@@H:46]1[CH2:41][CH2:34][CH2:33][N:32]1[C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[C@@H:44]([CH3:43])[C:6]([NH:7][C@@H:8]([CH:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)=[O:10])=[O:24]

Komponenten

5

Edukt 4

HCID 6422Trifluoroacetic acidHCID 2761487Boc-L-3,3-DiphenylalanineHCID 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 89642541tert-Butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3,3-diphenylpropan-2-yl]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 N-(tert-butoxycarbonyl)-β-phenyl-L-phenylalanine 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-e9d9148abc214fbd923cf0ea36947272
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722629B2

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