Hydrochloric Acid → (2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid

HRID 1411330Notes

Reaction equation

HRID 1411330 reaction equation
[NH2:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[OH-].[Na+].[CH3:11][O:12][C:13](Cl)=[O:14].Cl>O>[CH3:11][O:12][C:13]([NH:1][C@@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6287L-ValineHCID 6586Methyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidYield 67.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (S)-2-amino-3-methyl-butyric acid (10 g, 85 mmol), NaOH (10.3 g, 255 mmol) in water (100 mL) was treated with methylchloridocarbonate (8 g, 85 mmol) at 0° C. The reaction mixture was stirred for 24 h at room temperature and then 5 N aqueous HCl was added to the reaction mixture to adjust pH to 4. The mixture was filtered through a pad of Celite to give the product (10 g, 67% yield) as a white solid. 1H NMR (CH3OD, 400 MHz) δ (ppm) 4.05 (d, 1H), 3.65 (s, 3H), 2.14 (m, 1H), 0.95 (m, 6H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite

Sources & evidence

ORD record
ord-549fdd0be8914eabac9df229dd6bd5f5
Source dataset
uspto-grants-2014_12
Patent number
US08921372B2

Reaction notes

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