Acetone → HCID 10989578、化合物

HRID 1393466ノート

反応式

HRID 1393466 の反応式
[NH2:1][C@H:2]([C:7]([O:9]C)=[O:8])CC([O-])=O.[C:11]([O-])([O-])=[O:12].[Na+].[Na+].[C:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.C[C:30]([CH3:32])=[O:31]>O>[CH3:11][O:12][C:30](=[O:31])[CH2:32][CH:2]([NH:1][C:25](=[O:26])[CH2:24][CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]([OH:9])=[O:8]

参加物

7

反応物 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 64801Benzenepropanoyl chlorideHCID 57352248(3S)-3-Amino-4-methoxy-4-oxobutanoate

生成物 1

HCID 10989578HCID 10989578、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

Methyl L-aspartate (15.0 g, 0.082 mol), DI water (245 mL), acetone (20 mL), and Na2CO3 (30.8 g, 0.286 mol) were combined and cooled the solution to 5° C. 3-Phenyl-propionyl chloride (13.3 mL, 0.089 mol) was added dropwise via addition funnel over 10 min. The reaction was allowed to warm to ambient temperature and stir for 2 h. The reaction became very thick during this time. Added conc. HCl (50 mL) to the slurry until the pH was ≦4.0. The reaction mixture was extracted with CH2Cl2 (3×). The organic phase was washed with water and then dried (MgSO4), filtered and concentrated under reduced pressure. The clear, colorless oil was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.92 (br s, 1H), 7.28-7.17 (m, 5H), 6.57 (d, J=7.6 Hz, 1H), 4.87 (m, 1H), 3.67 (s, 3H), 2.96 (t, J=7.6 Hz, 2H), 2.89 (A of ABX, JAB=17.6 Hz, JAX=4.8 Hz, 1H), 2.88 (B of ABX, JBA=17.6 Hz, JBX=4.0 Hz, 1H), 2.69 (t, J=7.6 Hz, 2H); MS (EI+) 280 (M+H), 302 (M+H+Na).

後処理

  1. temperatureto warm to ambient temperature
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×)
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe clear, colorless oil was used without further purification

出典と根拠

ORDレコード
ord-38be6efefd9946c2bffdd8636e17ba3c
出典データセット
uspto-grants-2008_03
特許番号
US07345070B2

反応ノート

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