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 1022521Notes

Reaction equation

HRID 1022521 reaction equation
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]

Participants

5

Reactant 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×

Product 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

Procedure

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.

Workup

  1. customThe end product was purified by preparative HPLC

Sources & evidence

ORD record
ord-e9d9148abc214fbd923cf0ea36947272
Source dataset
uspto-grants-2014_05
Patent number
US08722629B2

Reaction notes

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