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 1022520Notes

Reaction equation

HRID 1022520 reaction equation
[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]

Participants

5

Reactant 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×

Product 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

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)-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.

Workup

  1. customThe end product was purified by preparative HPLC

Sources & evidence

ORD record
ord-617254b26bd64986962769114838a5fd
Source dataset
uspto-grants-2014_05
Patent number
US08722629B2

Reaction notes

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