1-Pyrrolidineethanamine → HCID 178512240, 화합물

HRID 1270986노트

반응식

HRID 1270986 반응식
C(O[C:6](=O)[NH:7][C@@H:8]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:9][C:10](=[O:19])[NH:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)(C)(C)C.C(OC(N[C@@H]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)CC(O)=O)=O)(C)(C)C.N1(CCN)CCCC1.[CH:54]1[CH:55]=[CH:56][C:57]2[N:62](O)N=N[C:58]=2[CH:59]=1.CN1CCOCC1.CC[N:73]=[C:74]=[N:75]CCCN(C)C.Cl>CN(C=O)C.O>[C:54]1([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:59]=[CH:58][C:57]([N:62]=[C:6]([NH:75][C:74]#[N:73])[NH:7][C@@H:8]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:9][C:10]([NH:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)=[O:19])=[CH:56][CH:55]=1

참가 물질

9

반응물 6

HCID 13441-PyrrolidineethanamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009108(3R)-3-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoic acidHCID 69430297HCID 69430297, 화합물

생성물 1

HCID 178512240HCID 178512240, 화합물수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

[(R)-1-Phenyl-2-(2-pyrrolidin-1-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester. To a solution of (R)-3-tert-butoxycarbonylamino-3-phenyl-propionic acid (0.54 g, 2.04 mmol), 2-pyrrolidin-1-yl-ethylamine (0.35 g, 3.06 mmol), HOBt (0.41 g, 3.06 mmol) and 4-methylmorpholine (0.41 g, 4.08 mmol) in DMF (10 mL), was added EDCl (0.59 g, 3.06 mmol), and the resulting solution was stirred under N2 at rt for 20 h. The solution was diluted with H2O (75 mL) and was extracted with EtOAc (3×75 mL). The combined extracts were washed with brine (100 mL), dried (Na2SO4) and filtered, and the solvent was removed. The crude product was purified by column chromatography on silica gel using a gradient of 2–30% (MeOH (1% NH4OH)/CH2Cl2) to afford 0.65 g. (88%) of the desired product as a white solid. Rf=0.34 (10% MeOH (1% NH4OH)/CH2Cl2). MS (electrospray): mass calculated for C20H31N3O3, 361.24; m/z found, 362.2 [M+H]+, 745.4 [2M+Na]+. 1H NMR (400 MHz, CDCl3): 7.32–7.28 (m, 4H), 7.24–7.20 (m, 1H), 6.37 (br s, 1H), 6.14 (br s, 1H), 5.01 (br s, 1H), 3.21 (dd, J=11.2, 5.7 Hz, 2H), 2.74–2.67 (m, 1H), 2.59 (dd, J=14, 5.9 Hz, 1H), 2.49–2.38 (m, 6H), 1.76–1.67 (m, 4H), 1.41 (s, 9H).

후처리

  1. extractionwas extracted with EtOAc (3×75 mL)
  2. washThe combined extracts were washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe crude product was purified by column chromatography on silica gel using a gradient of 2–30% (MeOH (1% NH4OH)/CH2Cl2)
  7. customto afford 0.65 g

출처 및 근거

ORD 기록
ord-2a19ea2444c442e6bb60b545c712c636
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202269B2

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