Isopropylamine → 1-(diphenylmethyl)-N-(1-methylethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxamide

HRID 605718노트

반응식

HRID 605718 반응식
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:8]2[CH2:11]C(NCC3C=CC=CC=3)(C(O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:32](CC)[CH:33]([CH3:35])[CH3:34])(C)C.C[CH:39]([NH2:41])[CH3:40].C([O:45][CH2:46][CH3:47])(=O)C>CN(C=O)C>[C:23]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][C:47]([NH:41][CH2:39][C:40]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)([C:46]([NH:32][CH:33]([CH3:34])[CH3:35])=[O:45])[CH2:11]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 6363IsopropylamineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 219058151-(Diphenylmethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxylic acid

생성물 1

HCID 670518131-(diphenylmethyl)-N-(1-methylethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxamide수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 1-(diphenylmethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxylic acid (0.50 g, 1.34 mmol), N,N-diisopropylethylamine (0.47 mL, 2.68 mmol) in DMF (3 mL) was added 1-benzotriazolyloxytripyrrolidinylphosphonium hexafluorophosphate (1.34 g, 2.68 mol) and the resulting mixture was stirred at room temperature for 10 minutes. To this mixture was added 2-propylamine (0.22 mL, 2.68 mmol) and stirring was continued for 18 h. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with 2% aqueous citric acid, 5% lithium chloride, and brine solutions (50 mL each), dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, eluting with 15-25% ethyl acetate-hexane) to give 1-(diphenylmethyl)-N-(1-methylethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxamide (0.51 g, 92% yield), MS (EI) for C27H31N3O: 414 (MH+).

후처리

  1. stirringstirring
  2. waitwas continued for 18 h
  3. washwashed with 2% aqueous citric acid, 5% lithium chloride, and brine solutions (50 mL each)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily residue which
  8. customwas purified by flash chromatography (silica gel, eluting with 15-25% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-7e4ddb508c3e4d3cad0c8c33d2ab14bc
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915250B2

반응 노트

불러오는 중…