Triethylamine → ((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxopiperidin-3-yl)methyl methanesulfonate

HRID 932273ノート

反応式

HRID 932273 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C@@:9]1([CH2:42][OH:43])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:11]([C@@H:29]([CH2:39][CH3:40])[CH2:30][N:31]([CH3:38])[S:32]([CH:35]2[CH2:37][CH2:36]2)(=[O:34])=[O:33])[C:10]1=[O:41])[CH:7]=[CH2:8].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:43][CH2:42][C@:9]1([CH2:6][CH:7]=[CH2:8])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:11]([C@@H:29]([CH2:39][CH3:40])[CH2:30][N:31]([CH3:38])[S:32]([CH:35]2[CH2:37][CH2:36]2)(=[O:33])=[O:34])[C:10]1=[O:41])(=[O:4])=[O:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68000440N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(hydroxymethyl)-2-oxopiperidin-1-yl)butyl)-N-methylcyclopropanesulfonamide

生成物 1

HCID 58573447((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-(N-methylcyclopropanesulfonamido)butan-2-yl)-2-oxopiperidin-3-yl)methyl methanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Methanesulfonyl chloride (0.200 ml, 2.59 mmol) was added to a solution of N-((S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(hydroxymethyl)-2-oxopiperidin-1-yl)butyl)-N-methylcyclopropanesulfonamide (1.0 g, 1.725 mmol) and triethylamine (0.480 ml, 3.45 mmol) in DCM. The reaction was stirred for 2 hours. The reaction mixture was diluted with DCM and washed with HCl (1N) and satd NaCl and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as an oil. The product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g), eluting with a gradient of 0% to 80% EtOAc in hexane, to provide the title compound as an oil. Mass Spectrum (ESI) m/z=657.2 (M+1).

後処理

  1. washwashed with HCl (1N) and satd NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo
  5. customto give the crude material as an oil
  6. customThe product was purified by chromatography through a RediSep® pre-packed silica gel column (Teledyne Isco, Lincoln, Nebr.) (12 g)
  7. washeluting with a gradient of 0% to 80% EtOAc in hexane

出典と根拠

ORDレコード
ord-ecc031e1915541a7bb6301a3e8995579
出典データセット
uspto-grants-2016_03
特許番号
US09296736B2

反応ノート

読み込み中…