Methanol → methyl (2S)-4-methyl-2-(methylamino)pentanoate

HRID 1977481Notes

Reaction equation

HRID 1977481 reaction equation
[CH3:1][NH:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].O1CCOC[CH2:12]1.CO>Cl>[CH3:12][O:9][C:8](=[O:10])[C@H:3]([CH2:4][CH:5]([CH3:7])[CH3:6])[NH:2][CH3:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 312751,4-DioxaneHCID 2777993N-Methylleucine

Product 1

HCID 10921446methyl (2S)-4-methyl-2-(methylamino)pentanoateYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

N-methyl-L-leucine (1.3 g, 8.95 mmol) was dissolved in 4M HCl, 1,4-dioxane (10 mL) and methanol (10 mL). The solution was stirred overnight at room temperature, then concentrated to afford the title compound as a white solid (100%). MS (ESI): 160.0 (M+H)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-b4ce263540d94618806501545f1348fd
Source dataset
uspto-grants-2001_05
Patent number
US06232342B1

Reaction notes

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