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

HRID 1629785ノート

反応式

HRID 1629785 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-83a9b17334c149558e2297885d4429fc
出典データセット
uspto-grants-2014_07
特許番号
US08791091B2

反応ノート

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