5-Hexenoyl chloride → N-[(Hex-5-en-1-yl)(methyl)carbamoyl]-3-methyl-L-valine

HRID 2377616Notes

Reaction equation

HRID 2377616 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C@@H:3]([C:14]([OH:16])=[O:15])[NH:4][C:5]([N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[O:6].[C:19](Cl)(=O)CCCC=C>>[CH3:1][C:2]([CH3:18])([CH3:17])[C@@H:3]([C:14]([OH:16])=[O:15])[NH:4][C:5]([N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:19])=[O:6]

Participants

3

Reactant 2

HCID 109755195-Hexenoyl chlorideHCID 574311913-Methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valine

Product 1

HCID 57431192N-[(Hex-5-en-1-yl)(methyl)carbamoyl]-3-methyl-L-valine

Procedure

3-Methyl-N-{[methyl(hex-5-enyl)amino]carbonyl}-L-valine was prepared according to the procedure for 3-methyl-N-{[methyl(pent-4-enyl)amino]carbonyl}-L-valine (Steps 1-5) by using 5-hexenoyl chloride instead of 4-pentenoyl chloride in Step 1. LRMS (ESI) m/z 271 [(M+H)+; calcd for C14H27N2O3: 271].

Sources & evidence

ORD record
ord-1ad30dff3fab40ff956ae072b8b8448e
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

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