反応式
[CH3:1][C:2]([S:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:7])[CH2:3][C:4]([OH:6])=O.ClC(Cl)(Cl)C(C(Cl)(Cl)Cl)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.C(N(CC)CC)C>C(Cl)Cl>[OH:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][N:51]([C:4](=[O:6])[CH2:3][C:2]([CH3:1])([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:7])[CH2:50][CH2:49]1参加物
反応物 5
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
A mixture of 3-methyl-3-(phenylmethylthio)butanoic acid (1 g, 4.6 mmol) and hexachloroacetone were dissolved in CH2Cl2 (20 mL) and cooled to −78° C. Triphenyl phosphine was added and the mixture was stirred for 30 minutes. Hydroxyethyl piperazine (550 μL, 4.5 mmol) was added in CH2Cl2 (10 mL) dropwise. Triethylamine (630 μL, 4.5 mmol) was added in CH2Cl2 (10 mL) dropwise. The cold bath was removed and the solution was stirred for 24 hours. The solvent was evaporated. The crude mixture was poured into 1N HCl (100 mL) and washed with Et2O (2×50 mL). The aqueous layer was made basic with 10% K2CO3 in a brine solution. The product was extracted with EtOAc (3×100 mL), dried over Na2SO4, and concentrated. This gave the title compound which was used immediately in the next reaction. 1H NMR (300 MHz, CDCl3) δ 7.18-7.37 (mult, 5H), 3.8 (s, 2H), 3.6 (t, J=5 Hz, 4H), 3.4 (t, J=5 Hz, 2H), 2.45-2.65 (mult, 8H), 1.5 (s, 6H).
後処理
- customThe cold bath was removed
- stirringthe solution was stirred for 24 hours
- customThe solvent was evaporated
- additionThe crude mixture was poured into 1N HCl (100 mL)
- washwashed with Et2O (2×50 mL)
- extractionThe product was extracted with EtOAc (3×100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
出典と根拠
- ORDレコード
- ord-eb9cbb1a2ec949a9b73c876803e04281
- 出典データセット
- uspto-grants-2001_10
- 特許番号
- US06297260B1
関連ノート
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