Methyl (S)-(-)-2-Isocyanato-3-methylbutyrate → Methyl N-{[(1,1-dimethylpent-4-en-1-yl)amino]carbonyl}-L-valinate

HRID 1095289Notes

Reaction equation

HRID 1095289 reaction equation
[O:1]=[C:2]=[N:3][C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]([CH3:7])[CH3:6].[CH3:12][C:13]([NH2:19])([CH2:15][CH2:16][CH:17]=[CH2:18])[CH3:14]>C1COCC1>[CH3:12][C:13]([NH:19][C:2]([NH:3][C@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]([CH3:6])[CH3:7])=[O:1])([CH3:14])[CH2:15][CH2:16][CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 10397066Methyl (S)-(-)-2-Isocyanato-3-methylbutyrateHCID 122640132-Methylhex-5-en-2-amine

Product 1

HCID 86648928Methyl N-{[(1,1-dimethylpent-4-en-1-yl)amino]carbonyl}-L-valinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl N-(oxomethylene)-L-valinate (2.80 g, 17.7 mmol) was added to 2-methylhex-5-en-2-amine [J. Org. Chem. (1976) 41(5) 855-863.] (2.00 g, 17.7 mmol) in THF (15 mL). After 5 minutes, the reaction mixture was evaporated to give the title compound as a solid, which was triturated with hexane and isolated by filtration (2.71 g). LRMS (M+H)+=271.4.

Workup

  1. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-6706af7e05b24ec881fbeb3227518113
Source dataset
uspto-grants-2012_03
Patent number
US08138164B2

Reaction notes

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