N-methylpent-4-en-1-amine → Methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate

HRID 1360106Notes

Reaction equation

HRID 1360106 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[N:8]([C@@H:11]([CH:16]([CH3:18])[CH3:17])[C:12]([O:14][CH3:15])=[O:13])=[C:9]=[O:10]>C1COCC1>[CH3:17][CH:16]([CH3:18])[C@H:11]([NH:8][C:9]([N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7])=[O:10])[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 541660N-methylpent-4-en-1-amineHCID 10397066Methyl (S)-(-)-2-Isocyanato-3-methylbutyrate

Product 1

HCID 57617072Methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried 500 mL round bottom flask under nitrogen was charged with THF (20 mL), N-methylpent-4-en-1-amine (Org. Lett. (2005), 7(9), pp 1737-1739) (1.0 g, 10.1 mmol) and methyl (2S)-2-isocyanato-3-methylbutanoate (J.O.C. (1992), 57(26), pp 7364-7366) (1.60 g, 10.1 mmol). Contents of the reaction flask were stirred at RT for 2 hours then rotary evaporated to afford the title compound as a colorless oil. LRMS m/e [M+H]+ 257.

Workup

  1. customthen rotary evaporated

Sources & evidence

ORD record
ord-0eb8344d0b3a4424b510b3d72ba52fd4
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

Loading…