Pyrrolidine → HCID 57571228、化合物

HRID 2065852ノート

反応式

HRID 2065852 の反応式
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[N:22]([CH:26]([CH3:28])C)[CH:23]([CH3:25])C.ClC(OCC(C)C)=O.N1CCCC1>C(Cl)Cl>[O:19]=[C:17]([N:22]1[CH2:23][CH2:25][CH2:28][CH2:26]1)[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1

参加物

6

反応物 4

HCID 31268PyrrolidineHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 7020844(2S)-2-(((tert-butoxy)carbonyl)amino)-3-(pyridin-4-yl)propanoic acid

生成物 1

HCID 57571228HCID 57571228、化合物収率 24.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

N-Boc-(S)-3-(pyridin-4-yl)alanine (0.500 g, 1.88 mmol) was dissolved in CH2Cl2 (15 mL) and DIEA (361 μL, 2.07 mmol) was added. The mixture was cooled to 0° C. and isobutyl chloroformate (270 μL, 2.07 mmol) was added. The mixture was stirred for 10 min and pyrrolidine (267 mg, 3.76 mmol) in CH2Cl2 (5 mL) was added. This mixture was stirred for 15 min at 4° C., 12 h at 25° C., washed successively with NaH2PO4, saturated sodium hydrogen carbonate, water and brine. The organic layer was dried over magnesium sulfate and evaporated to dryness. The residue obtained was purify by column chromatography (SiO2) using a gradient of MeOH 0-10% [v/v] in EtOAc to give tert-butyl (R)-1-oxo-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-2-ylcarbamate EBE 06172 (146 mg, 24% yield) as a white solid.

後処理

  1. stirringThis mixture was stirred for 15 min at 4° C., 12 h at 25° C.
  2. washwashed successively with NaH2PO4, saturated sodium hydrogen carbonate, water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue obtained
  6. customwas purify by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-a75182c0d5ba4584a709a996ee5370ef
出典データセット
uspto-grants-2012_10
特許番号
US08288556B2

反応ノート

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