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

HRID 1177867

반응식

HRID 1177867 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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 (

출처 및 근거

ORD 기록
ord-f1f218a33cc446d9b8b3a6fd70f94fd0
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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