반응 #1109702

ord-617254b26bd64986962769114838a5fd

반응 방정식

CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCCCO1
Material 5
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCCCO1
tert-butyl[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate
CC[C@H](C)[C@@H]([C@@H](CC(=O)OC(C)(C)C)OC)N(C)C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C
Material 1
CC[C@H](C)[C@@H]([C@@H](CC(=O)OC(C)(C)C)OC)N(C)C(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C
tert-butyl (3R,4S,5S)-4-[{N-[(benzyloxy)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate
O=C(O)C(F)(F)F
trifluoroacetic acid
CC(C)(C)OC(=O)N[C@H](C(=O)O)C(C)(C)C
N-(tert-butoxycarbonyl)-3-methyl-L-valine
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCCCO1
Intermediates 5
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCCCO1
tert-butyl[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCCCO1
1,2-oxazinane hydrochloride
CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCCCO1
tert-butyl[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]carbamate
CO[C@H]([C@@H](C)C(=O)N[C@H](C(=O)N1CCCCO1)C(C)(C)C)[C@@H]1CCCN1C(=O)OC(C)(C)C
title compound
CO[C@H]([C@@H](C)C(=O)N[C@H](C(=O)N1CCCCO1)C(C)(C)C)[C@@H]1CCCN1C(=O)OC(C)(C)C
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

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타The end product was purified by preparative HPLC

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08722629B2uspto-grants-2014_05