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

HRID 1897558노트

반응식

HRID 1897558 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)).

후처리

  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)

출처 및 근거

ORD 기록
ord-4a5d63d830d0428bbf1c5b2d73612444
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519137B2

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