4-Methylmorpholine → Benzyl (2R)-2-Benzyl-3-(4-trifluoroethylpiperazin-1-ylcarbonyl)propionate

HRID 973498ノート

反応式

HRID 973498 の反応式
[C:1]([CH2:4][C@@H:5]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])([OH:3])=O.CN1CCOCC1.ClC(OCC(C)C)=O.[F:38][C:39]([F:48])([F:47])[CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>C(Cl)Cl>[CH2:16]([C@H:5]([CH2:4][C:1]([N:44]1[CH2:43][CH2:42][N:41]([CH2:40][C:39]([F:47])([F:48])[F:38])[CH2:46][CH2:45]1)=[O:3])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 95339211-(2,2,2-Trifluoroethyl)piperazineHCID 14213081(R)-2-Benzyl-succinic acid 1-benzyl ester

生成物 1

HCID 15018098Benzyl (2R)-2-Benzyl-3-(4-trifluoroethylpiperazin-1-ylcarbonyl)propionate収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

The resultant acid from Example 23 (0.500 g, 1.68 mmol) in CH2Cl2 (7 ml) at -10° C. was treated with N-methylmorpholine (0.20 ml, 1.82 mmol) and then isobutyl chloroformate (0.22 ml, 1.68 mmol). After 5 min 1-trifluoroethylpiperazine (0.30 g, 1.78 mmol) was added and the mixture was stirred at -10° C. for 15 min and then at room temperature for 2 h. The solvent was evaporated and the residue was taken up in ethyl acetate which was washed with saturated NaHCO3 solution, water and brine, and then dried over Na2SO4 and evaporated. Chromatography of the residue on silica gel with 20-33% ethyl acetate in hexane provided 0.61 g (81%) of an oil. 1H NMR (CDCl3) δ7.10-7.40 (m,10H), 5.15 (d,1H), 5.05 (d,1H), 3.25-3.70 (m,5H), 3.04 (dd,1H), 2.97 (q,2H), 2.81 (dd,1H), 2.72 (dd,1H), 2.60 (m,4H), 2.32 (dd,1H).

後処理

  1. waitat room temperature for 2 h
  2. customThe solvent was evaporated
  3. washwas washed with saturated NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

出典と根拠

ORDレコード
ord-ff54ee1375de4638bbbcab286e398732
出典データセット
uspto-grants-1991_11
特許番号
US05063208

反応ノート

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