N-methylpent-4-en-1-amine → Methyl 3-methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valinate

HRID 1423351Notes

Reaction equation

HRID 1423351 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[CH3:8][C:9]([CH3:19])([CH3:18])[C@@H:10]([C:14]([O:16][CH3:17])=[O:15])[N:11]=[C:12]=[O:13]>C1COCC1>[CH3:8][C:9]([CH3:19])([CH3:18])[C@@H:10]([C:14]([O:16][CH3:17])=[O:15])[NH:11][C:12]([N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7])=[O:13]

Participants

4

Reactant 2

HCID 541660N-methylpent-4-en-1-amineHCID 59856496methyl (2S)-2-isocyanato-3,3-dimethylbutanoate

Product 1

HCID 59856469Methyl 3-methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methylpent-4-en-1-amine (ref: Org. Biomol. Chem.; EN; 2; 20; 2004; 3006-3017) (2.0 g, 21.2 mmol) in THF (20 mL) was added methyl 3-methyl-N-(oxomethylene)-L-valinate (Ref: EP 0 486 948 A2) (3.5 g, 20.2 mmol). After 2 h, the solvent was removed in vacuo and the crude material was purified on silica (40% EtOAc/hexanes) to yield the title compound. LRMS (M+H)+ 271.3

Workup

  1. customthe solvent was removed in vacuo
  2. customthe crude material was purified on silica (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cc99e92191a1456bbcd93c9aac3a2064
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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