Diethyl Ether → Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetate

HRID 1048448ノート

反応式

HRID 1048448 の反応式
[Si]([O:18][CH2:19][C@@H:20]([N:23]1[C@H:28]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C@@H:27]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)[CH2:26][C@@:25]([CH2:44][C:45]([OH:47])=[O:46])([CH3:43])[C:24]1=[O:48])[CH2:21][CH3:22])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:49][Si](C=[N+]=[N-])(C)C.C(OCC)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CO.C1C=CC=CC=1.C1COCC1>[Cl:42][C:38]1[CH:37]=[C:36]([C@@H:27]2[C@@H:28]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[N:23]([C@@H:20]([CH2:21][CH3:22])[CH2:19][OH:18])[C:24](=[O:48])[C@:25]([CH2:44][C:45]([O:47][CH3:49])=[O:46])([CH3:43])[CH2:26]2)[CH:41]=[CH:40][CH:39]=1

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 2724141Tetrabutylammonium FluorideHCID 601541832-((3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic acid

生成物 1

HCID 58573771Methyl 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methyl-2-oxopiperidin-3-yl)acetate

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-((3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-3-yl)acetic acid (Example 185) in MeOH (2 mL) and benzene (8 mL) was stirred with (trimethylsilyl)diazomethane, 2.0 M in diethyl ether (2.02 mL, 4.04 mmol) at rt for 0.5 h. After that time the mixture was concentrated to give the crude methyl ester, which was treated with TBAF in THF at rt for 30 h. The mixture was concentrated and purified by chromatography on silica gel (0 to 100% EtOAc in hexanes) to give the title compound. Mass Spectrum (ESI) m/z=478 (M+1).

後処理

  1. concentrationAfter that time the mixture was concentrated
  2. customto give the crude methyl ester, which
  3. concentrationThe mixture was concentrated
  4. custompurified by chromatography on silica gel (0 to 100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-5043a48901c0476f94b5c67808538100
出典データセット
uspto-grants-2013_10
特許番号
US08569341B2

反応ノート

読み込み中…