4-Methylmorpholine → N-[(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl carbamoyl)-methyl]-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propionamide

HRID 2110551노트

반응식

HRID 2110551 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][C:11]([OH:13])=O.[NH2:20][CH2:21][C:22]([NH:24][CH:25]1[CH:30]2[CH:26]1[CH2:27][N:28]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:29]2)=[O:23].C(OC(NCC(O)=O)=O)(C)(C)C.C(N1CC2C(C2N)C1)C1C=CC=CC=1.CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH2:31]([N:28]1[CH2:27][CH:26]2[CH:30]([CH:25]2[NH:24][C:22]([CH2:21][NH:20][C:11](=[O:13])[CH2:10][CH:9]([C:3]2[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=2[OH:1])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:23])[CH2:29]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

9

반응물 6

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 125220763-(2-Hydroxy-5-methylphenyl)-3-phenyl propionic acidHCID 185069973-Benzyl-3-azabicyclo(3.1.0)hexan-6-amineHCID 688714602-amino-N-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-acetamide

생성물 1

HCID 68870343N-[(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl carbamoyl)-methyl]-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propionamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

The compound, 3-(2-hydroxy-5-methylphenyl)-3-phenyl propionic acid (198 mg, 0.77 mmole, 1 eq) and 2-amino-N-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-acetamide, 200 mg, 0.179 mmole, 1 eq prepared by reacting t-butoxy carbonylamino-acetic acid with 3-benzyl-3-azabicylo[3.1.0]hex-6-yl amine, which in turn, was prepared following the procedure of T. F. Braish et al., Synlett, 1996, 1100) were dissolved in dimethylformamide (3 ml). The reaction mixture was cooled to 0° C. with subsequent addition of N-methyl morpholine (2.31 mmole, 3 eq) and HOBT (0.77 mmole, 1 eq). The resulting reaction mixture was stirred for 1 hour at the same temperature and then at room temperature. The reaction mixture was diluted with water and extracted the organic compound with ethyl acetate. The solvent was removed under reduced pressure and dried. The crude compound was purified by column chromatography using ethyl acetate, methanol and dichloromethane solvent system.

후처리

  1. customwas prepared
  2. customThe resulting reaction mixture
  3. customat room temperature
  4. extractionextracted the organic compound with ethyl acetate
  5. customThe solvent was removed under reduced pressure
  6. customdried
  7. customThe crude compound was purified by column chromatography

출처 및 근거

ORD 기록
ord-5051d87ec9f945ac8a6165eb78ae3f80
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517905B2

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