1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 1177867

反応式

HRID 1177867 の反応式
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([NH:17][CH2:18][C:19]([OH:21])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[N:44]1([C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]([F:61])([F:60])[F:59])=[O:51])[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>CN(C=O)C.CCCCCC.O>[C:10]([O:14][C:15](=[O:16])[NH:17][CH2:18][C:19](=[O:21])[N:47]1[CH2:48][CH2:49][N:44]([C:50](=[O:51])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]([F:61])([F:59])[F:60])[CH2:45][CH2:46]1)([CH3:11])([CH3:12])[CH3:13]

参加物

9

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochloride

生成物 1

HCID 59559599{2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester収率 96%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

DIPEA (3.5 mL, 20.41 mmol) was added dropwise to tert-butoxycarbonylamino-acetic acid (1.42 g, 8.16 mmol) in DMF (15 mL). EDCI (2.6 g, 13.61 mmol) and HOBT (1.1 g, 8.16 mmol) were added consecutively and, after 10 mins, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (2 g, 6.80 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was then added and the product was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 3.3 g of crude product. Purification by column chromatography (using silica gel of mesh size of 60-120 and 60/40 EtOAc:hexane as the eluent) afforded 2.6 g (96% yield) of {2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester.

後処理

  1. extractionthe product was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford 3.3 g of crude product
  6. customPurification by column chromatography (

出典と根拠

ORDレコード
ord-f1f218a33cc446d9b8b3a6fd70f94fd0
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

関連ノート

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