1,1'-Carbonyldiimidazole → benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate

HRID 1254376ノート

反応式

HRID 1254376 の反応式
[CH2:1]([O:8][C:9](=[O:21])[N:10]([CH2:12][CH:13]([NH2:20])[CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:27]([N:29]2[CH:33]=N[CH:31]=[CH:30]2)=[O:28])C=1.CCN(C(C)C)C(C)C.[O:43]1[C:47]2[C:48]([C@:52]([C@@H:60]3CCCN[CH2:61]3)([OH:59])[CH2:53][CH2:54][CH2:55][CH2:56][O:57][CH3:58])=[CH:49][CH:50]=[CH:51][C:46]=2[CH:45]=[CH:44]1>C(Cl)Cl>[O:43]1[C:47]2[C:48]([C@:52]([C@@H:60]3[CH2:61][CH2:31][CH2:30][N:29]([C:27]([NH:20][C@@H:13]([CH2:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19]4)[CH2:12][N:10]([CH3:11])[C:9](=[O:21])[O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:28])[CH2:33]3)([OH:59])[CH2:53][CH2:54][CH2:55][CH2:56][O:57][CH3:58])=[CH:49][CH:50]=[CH:51][C:46]=2[CH:45]=[CH:44]1

参加物

6

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 59382903(S)-1-(benzofuran-7-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-olHCID 67189318HCID 67189318、化合物

生成物 1

HCID 57544782benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate収率 51.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (2-amino-3-cyclopentyl-propyl)-methyl-carbamic acid benzyl ester (87 mg, 0.3 mmol) and CDI (48.6 mg, 0.3 mmol) in CH2Cl2 (5 mL) cooled to 0-5° C. was added DIEA (0.5 mL). After stirring for 30 minutes, a solution of (S)-1-(benzofuran-7-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol (95.1 mg, 0.3 mmol) in CH2Cl2 (3 mL) was added dropwise. The reaction mixture was allowed to warm to rt and stirred overnight. The mixture was washed with water (10 mL). The aqueous layer was extracted with CH2Cl2 (2×15 mL) and the combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by prep HPLC to give benzyl (S)-2-((R)-3-((S)-1-(benzofuran-7-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)-3-cyclopentylpropylmethylcarbamate (98.5 mg, 51.9%).

後処理

  1. stirringstirred overnight
  2. washThe mixture was washed with water (10 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×15 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by prep HPLC

出典と根拠

ORDレコード
ord-af1c064241c14c639b89ea56adcdfe40
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

読み込み中…