Ethyl 1-(3-butenyl)cyclopropanecarboxylate → N-({[1-(But-3-en-1-yl)cyclopropyl]methoxy}carbonyl)-3-methyl-L-valine

HRID 1511577Notes

Reaction equation

HRID 1511577 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].C(C1(C(OCC)=O)CC1)CC=C>>[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][CH2:1]1)[CH2:17][CH:18]=[CH2:19]

Participants

3

Reactant 2

HCID 14217022Ethyl 1-(3-butenyl)cyclopropanecarboxylateHCID 45379499(S)-2-((((2,2-Dimethylhex-5-en-1-yl)oxy)carbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 45379500N-({[1-(But-3-en-1-yl)cyclopropyl]methoxy}carbonyl)-3-methyl-L-valine

Procedure

N-{[(1-But-3-en-1-ylcyclopropyl)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 (Steps 2 and 3) by using ethyl 1-but-3-en-1-ylcyclopropanecarboxylate-instead of ethyl 2,2-dimethylhex-5-enoate in Step 2. LRMS (ESI) m/z 284.3 [(M+H)+; calcd for C15H26NO4: 284.2].

Sources & evidence

ORD record
ord-da6f2d0836314801ae2762f07f91a81f
Source dataset
uspto-grants-2012_07
Patent number
US08216999B2

Reaction notes

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