1-Pyrrolidineethanamine → HCID 178512240、化合物

HRID 1270986ノート

反応式

HRID 1270986 の反応式
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

参加物

9

反応物 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、化合物

生成物 1

HCID 178512240HCID 178512240、化合物収率 88%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

[(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).

後処理

  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

出典と根拠

ORDレコード
ord-2a19ea2444c442e6bb60b545c712c636
出典データセット
uspto-grants-2007_04
特許番号
US07202269B2

反応ノート

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