ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

2-Methyl-6-nitrobenzoic anhydride → (3R,7S,10S,13R,14S)-7-benzyl-14-hydroxy-13-isopropyl-3-((E)-4-tritylsulfanyl-but-1-enyl)-10-tritylsulfanylmethyl-1,2-dioxa-4,9,12-triaza-cyclohexadecane-5,8,11,16-tetraone

HRID 888673
ノート
印刷プレビュー

反応式

HRID 888673 の反応式
CC1C=CC=C([N+]([O-])=O)C=1C(OC(C1C([N+]([O-])=O)=CC=CC=1C)=O)=O.[OH:26][C@H:27]([C@H:32]([NH:36][C:37](=[O:101])[C@H:38]([NH:60][C:61](=[O:100])[C@H:62]([CH2:70][C:71](=[O:99])[NH:72][C@H:73]([OH:98])/[CH:74]=[CH:75]/[CH2:76][CH2:77][S:78][C:79]([C:92]1[CH:97]=[CH:96][CH:95]=[CH:94][CH:93]=1)([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[CH2:39][S:40][C:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:33]([CH3:35])[CH3:34])[CH2:28][C:29]([OH:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:63]([C@@H:62]1[C:61](=[O:100])[NH:60][C@H:38]([CH2:39][S:40][C:41]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:37](=[O:101])[NH:36][C@H:32]([CH:33]([CH3:35])[CH3:34])[C@@H:27]([OH:26])[CH2:28][C:29](=[O:31])[O:30][O:98][C@H:73](/[CH:74]=[CH:75]/[CH2:76][CH2:77][S:78][C:79]([C:92]2[CH:93]=[CH:94][CH:95]=[CH:96][CH:97]=2)([C:86]2[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=2)[C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[NH:72][C:71](=[O:99])[CH2:70]1)[C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 104726482-Methyl-6-nitrobenzoic anhydrideHCID 86639715(3S,4R)-3-hydroxy-4-((S)-2-{(S)-2-[((E)-(R)-1-hydroxy-5-tritylsulfanyl-pent-2-enylcarbamoyl)-methyl]-3-phenyl-propionylamino}-3-tritylsulfanyl-propionylamino)-5-methyl-hexanoic acid

生成物 1

HCID 86639714(3R,7S,10S,13R,14S)-7-benzyl-14-hydroxy-13-isopropyl-3-((E)-4-tritylsulfanyl-but-1-enyl)-10-tritylsulfanylmethyl-1,2-dioxa-4,9,12-triaza-cyclohexadecane-5,8,11,16-tetraone収率 61.5%

試薬・触媒・溶媒 2

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

実験手順

To a solution of MNBA (54 mg, 0.16 mmol) and DMAP (38 mg, 0.31 mmol) in CH2Cl2 (29 mL) was added dropwise a solution of the acid 5A (137 mg, 0.13 mmol) in CH2Cl2 (117 mL) over 4.5 h, this was then stirred overnight at room temperature. The reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL) before being dried (MgSO4), filtered and concentrated in vacuo to give a brown solid. Purification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3) gave 6A (79.4 mg, 0.08 mmol, 58%) as a white/brown solid: Rf 0.14 EtOAc/Hexane (4:6).

後処理

  1. washThe reaction mixture was washed sequentially with HCl (1M, 40 mL), sodium hydrogen carbonate (40 ml) and sat. brine (40 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid
  6. customPurification by column chromatography on silica gel (eluent 4:6-1:1 EtOAc/Hexane increased to 1:9 MeOH/CHCl3)

出典と根拠

ORDレコード
ord-68cc2c44f0784ad9babe48ce1c1c8577
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08247372B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート