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Water → ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

HRID 1354547
ノート
印刷プレビュー

反応式

HRID 1354547 の反応式
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:5](=[O:17])[CH2:4]1)[CH3:2].Cl.[CH2:19](O)[CH3:20].[OH2:22]>C(OCC)(=O)C>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:11]=[CH:12][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([O:17][CH2:19][CH3:20])=[O:22])=[CH:8][CH:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 21887872Ethanol hydrochloride

生成物 1

HCID 57888577ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

To 200 mg (0.822 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6, 2.0 g (16.45 mmol) of 30 wt % hydrogen chloride/ethanol solution was added dropwise for 5 minutes. On completion of the addition, the resulting solution was heated to 40° C. and stirred for 14 hours. Water (5 mL) was added to the solution and extraction with ethyl acetate was carried out. The extracted organic layer was washed with saturated brine and the product was dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain ethyl (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoate as a yellow oil (193.8 mg, crude yield: 82%). 1H-NMR (CDCl3, 400 MHz/ppm): 6 0.98 (3H, t), 1.23 (3H, t), 1.55-1.71 (2H, m), 2.53 (2H, m), 3.75-3.82 (1H, m), 4.11 (2H, q), 6.61 (2H, d), 7.38 (2H, d)

後処理

  1. additionOn completion of the addition
  2. washThe extracted organic layer was washed with saturated brine
  3. dry with materialthe product was dried with anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-73fe19ce2e774848ad86095eb599e904
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07223859B2

反応ノート

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