Methyl cyclohexanecarboxylate → N-({[1-(But-3-en-1-yl)cyclohexyl]methoxy}carbonyl)-3-methyl-L-valine

HRID 1511573Notes

Reaction equation

[CH3:1][C:2]([CH3:20])([CH2:16][CH2:17][CH:18]=[CH2:19])[CH2:3][O:4][C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6].[CH:21]1(C(OC)=O)[CH2:26]CCC[CH2:22]1>>[CH2:16]([C:2]1([CH2:3][O:4][C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[C:9]([CH3:10])([CH3:11])[CH3:12])=[O:6])[CH2:20][CH2:26][CH2:21][CH2:22][CH2:1]1)[CH2:17][CH:18]=[CH2:19]

Participants

Reactant 2

HCID 20748Methyl cyclohexanecarboxylate

HCID 45379499(S)-2-((((2,2-Dimethylhex-5-en-1-yl)oxy)carbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 45379503N-({[1-(But-3-en-1-yl)cyclohexyl]methoxy}carbonyl)-3-methyl-L-valine

Procedure

N-{[(1-But-3-en-1-ylcyclohexyl)methoxy]carbonyl}-3-methyl-L-valine was prepared according to the procedure for N-{[(2,2-dimethylhex-5-enyl)oxy]carbonyl}-3-methyl-L-valine by using methyl cyclohexanecarboxylate instead of ethyl isobutyrate in Step 1. LRMS (ESI) m/z 326.3 [(M+H)+; calcd for C18H32NO4: 326.2].

Sources & evidence

ORD record: ord-557ceca2dc89454ca7dc13e5dca429a8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08216999B2

Reaction notes

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