Triethylamine → HCID 69620892、化合物

HRID 1628296ノート

反応式

HRID 1628296 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=2)[CH:7]=1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[C:4]([NH:15][C:16](=[O:33])[C@@H:17]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:3]=[C:2]([NH:1][S:42]([CH3:41])(=[O:44])=[O:43])[CH:7]=2)[CH:13]=[CH:12][N:11]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69620893HCID 69620893、化合物

生成物 1

HCID 69620892HCID 69620892、化合物収率 47.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 51.1D (512 mg, 1.16 mmol) and triethylamine (478 μl, 3.44 mmol) in CH2Cl2 (10 mL) under N2 was added methanesulfonyl chloride (available from Aldrich) (84.3 μl, 1.08 mmol) drop wise over 10 min. After stirring at 0° C. for 30 min, the reaction mixture was treated with saturated aqueous NaHCO3 (1 mL), diluted with water (10 mL), and extracted with CH2Cl2 (3×10 mL). Organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel using 0-70% EtOAc/CH2Cl2 provided title product 51.1E as white solid (268 mg, 43%).

後処理

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by flash chromatography on silica gel using 0-70% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-7304fb8d49a44900b78c100b2a3392af
出典データセット
uspto-grants-2014_07
特許番号
US08785468B2

反応ノート

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