Triethylamine → Methyl 3-oxo-2-(pivalamido)butanoate

HRID 1897558Notes

Reaction equation

HRID 1897558 reaction equation
Cl.[NH2:2][CH:3]([C:8](=[O:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5].[C:11](Cl)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[O:10]=[C:8]([CH3:9])[CH:3]([NH:2][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 23120881Methyl 2-amino-3-oxobutanoate hydrochloride

Product 1

HCID 57659743Methyl 3-oxo-2-(pivalamido)butanoateYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-amino-3-oxobutanoate hydrochloride (0.50 g, 3.0 mmol) in CH2Cl2 (30 mL) was cooled in an ice bath. Pivaloyl chloride (0.37 mL, 3.0 mmol) and triethylamine (0.84 mL, 6.0 mmol) were slowly added, and the reaction was allowed to slowly warm to room temperature overnight. The reaction was washed with water, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (0%-3% MeOH—CH2Cl2) to obtain methyl 3-oxo-2-(pivalamido)butanoate (0.48 g, 74% yield). 1H NMR (400 MHz, CDCl3) δ 6.82 (bs, 1H), 5.21 (d, J=6.1 Hz, 1H), 3.82 (s, 3H), 2.39 (s, 3H), 1.24 (s, 9H) ppm. LC/MS: m/z 216.5 (M+H)+ at 1.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. washThe reaction was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography (0%-3% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-4a5d63d830d0428bbf1c5b2d73612444
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

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