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 1022523Notes

Reaction equation

HRID 1022523 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@@: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]

Participants

5

Reactant 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×

Product 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

Procedure

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.

Workup

  1. customThe end product was purified by preparative HPLC

Sources & evidence

ORD record
ord-d526ba0a9af74003bc4599b3c4675786
Source dataset
uspto-grants-2014_05
Patent number
US08722629B2

Reaction notes

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