Ammonium Hydroxide → Ethyl 2-amino-2-methyl-4-oxo-4-p-tolylbutanoate

HRID 1629785노트

반응식

HRID 1629785 반응식
[CH3:1]/[C:2](=[CH:8]\[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH4+:18].[OH-]>CS(C)=O.CCOC(C)=O>[NH2:18][C:2]([CH3:1])([CH2:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

참가 물질

5

반응물 2

HCID 14923Ammonium HydroxideHCID 86685877(E)-Ethyl 2-methyl-4-oxo-4-p-tolylbut-2-enoate

생성물 1

HCID 86685876Ethyl 2-amino-2-methyl-4-oxo-4-p-tolylbutanoate수율 55.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Intermediate 102A (1.067 g, 4.59 mmol) in DMSO (20 mL) under argon was added NH4OH (18.04 mL, 271 mmol) and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc (75 mL) and washed sequentially with water (40 mL) and brine (20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo to give a yellow oil. The oil was purified by silica gel chromatography (120 g silica gel) to provide the desired product (0.632 g, 55%) as a clear oil. LCMS Anal. Calc'd for C14H19NO3 249.14, found [M+H] 250.1. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=8.25 Hz, 2H), 7.24 (d, J=7.98 Hz, 2H), 4.14 (dd, J=7.15, 2.75 Hz, 2H), 3.65 (d, J=17.61 Hz, 1H), 3.20 (d, J=17.61 Hz, 1H), 2.40 (s, 3H), 2.18-2.27 (m, 2H), 1.39 (s, 3H), 1.19 (t, J=7.01 Hz, 3H).

후처리

  1. washwashed sequentially with water (40 mL) and brine (20 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a yellow oil
  5. customThe oil was purified by silica gel chromatography (120 g silica gel)

출처 및 근거

ORD 기록
ord-83a9b17334c149558e2297885d4429fc
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791091B2

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