Methanesulfonyl chloride → 4-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

HRID 446962ノート

反応式

HRID 446962 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][NH:8][CH:7]2[CH2:10][CH2:11][N:12]([C:13](=[O:35])[CH:14]([NH:21][C:22](=[O:34])[CH:23]([N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:26])[CH3:24])[CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:6]12)=[O:4].CCN(C(C)C)C(C)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8]([S:46]([CH3:45])(=[O:48])=[O:47])[CH:7]2[CH2:10][CH2:11][N:12]([C:13](=[O:35])[CH:14]([NH:21][C:22](=[O:34])[CH:23]([N:25]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH3:26])[CH3:24])[CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:6]12)=[O:4]

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 672826294-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

生成物 1

HCID 672813824-{2-[2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester収率 100.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 19 (0.31 g, 0.63 mmol) in DCM (10 mL) was cooled to 0° C. and treated with DIPEA (0.2 mL, 1.2 mmol) and DMAP (5 mg, 0.04 mmol). Methanesulfonyl chloride (0.08 mL, 1 mmol) was added. After 2 h, the solution was diluted with DCM, washed successively with 1M HCl, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 20 as an orange-colored oil (362 mg) which was used without further purification.

後処理

  1. washwashed successively with 1M HCl, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-b3d93173e62443bcaf0407a9bae033c0
出典データセット
uspto-grants-2013_07
特許番号
US08481495B2

反応ノート

読み込み中…