1,2-Dichloroethane → (2R)-1-Benzyl-N-(3-hydroxy-4-oxo-1-phenyl-4-(pyridin-2-ylmethylamino)-butan-2-yl)-5-oxopyrrolidine-2-carboxamide

HRID 2061679ノート

反応式

HRID 2061679 の反応式
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:16][CH:17]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:18]([OH:22])[C:19](O)=[O:20])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][NH2:37].O.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.C(N(CC)CC)C>ClCCl>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:16][CH:17]([CH:18]([OH:22])[C:19](=[O:20])[NH:37][CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 666445723-((R)-1-Benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoic Acid

生成物 1

HCID 67095315(2R)-1-Benzyl-N-(3-hydroxy-4-oxo-1-phenyl-4-(pyridin-2-ylmethylamino)-butan-2-yl)-5-oxopyrrolidine-2-carboxamide収率 34%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoic acid (300 mg, 0.757 mmol) and pyridin-2-ylmethanamine (94 μl, 98 mg, 0.908 mmol) were dissolved in 13 ml dichloromethane and cooled to 5° C. At this temperature 1-hydroxybenzotriazole hydrate (127 mg, 0.832 mmol), EDC (160 mg, 0.832 mmol) and triethylamine (1.58 ml, 127 mg, 1135 mmol) were successively added. After stirring overnight at room temperature the reaction mixture was concentrated under reduced pressure, water was added and the mixture extracted three times with ethyl acetate. The combined organic layers were successively washed with aq. saturated NaHCO3 solution and brine, dried over Na2SO4 and the solvent was removed under reduced pressure. Column chromatography on silica gel using dichloromethane/MeOH (97/3), followed by dichloromethane/MeOH (95/5), resulted in the title compound (125 mg, yield: 34%) as a white powder.

後処理

  1. concentrationwas concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture extracted three times with ethyl acetate
  4. washThe combined organic layers were successively washed with aq. saturated NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-e2f17ca2aa7e4995804e116d02a8f7b5
出典データセット
uspto-grants-2012_10
特許番号
US08283363B2

反応ノート

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