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

HRID 1022520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022520
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20]C=1)C(N1CCCCO1)=O)([CH3:4])([CH3:3])[CH3:2].[C:25]([O:29]C(N[C@H](C(O)=O)C(C)(C)C)=O)(C)(C)C.F[C:42](F)(F)C(O)=O.C(O[C:56]([NH:58][C@H:59]([C:63]([N:65](C)[C@@H:66]([C@@H](C)CC)[C@H:67](OC)[CH2:68][C:69]([O:71]C(C)(C)C)=O)=[O:64])[CH:60]([CH3:62])[CH3:61])=[O:57])C1C=CC=CC=1>>[CH3:42][C:60]([CH3:61])([CH3:62])[C@H:59]([NH:58][C:56](=[O:57])[C@H:21]([CH3:20])[C@H:22]([C@@H:23]1[CH2:18][CH2:17][CH2:8][N:7]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])[O:29][CH3:25])[C:63]([N:65]1[CH2:66][CH2:67][CH2:68][CH2:69][O:71]1)=[O:64]

Komponenten

5

Edukt 4

HCID 6422Trifluoroacetic acidHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic 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 89642537tert-Butyl (2S)-2-[(1R,2R)-3-{[(2S)-3,3-dimethyl-1-(1,2-oxazinan-2-yl)-1-oxobutan-2-yl]amino}-1-methoxy-2-methyl-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)-3-methyl-L-valine 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-617254b26bd64986962769114838a5fd
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722629B2

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