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Potassium Carbonate → prop-2-enyl (6S,6aS)-3-[3-[[(6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-5-[[4-[[(2R)-2-[[(2R)-3-methyl-2-(prop-2-enoxycarbonylamino)butanoyl]amino]propanoyl]amino]phenyl]methoxycarbonyl]-11-oxo-8-[(E)-prop-1-enyl]-6a,7-dihydro-6H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-6-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-11-oxo-8-[(E)-prop-1-enyl]-6a,7-dihydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carboxylate

HRID 513365
ノート
印刷プレビュー

反応式

HRID 513365 の反応式
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:14][C@@H:15]1[N:21]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:50])[C@@H:34]([NH:36][C:37](=[O:49])[C@@H:38]([NH:42][C:43]([O:45][CH2:46][CH:47]=[CH2:48])=[O:44])[CH:39]([CH3:41])[CH3:40])[CH3:35])=[CH:28][CH:27]=2)=[O:23])[C:20]2[CH:51]=[C:52]([OH:57])[C:53]([O:55][CH3:56])=[CH:54][C:19]=2[C:18](=[O:58])[N:17]2[CH:59]=[C:60](/[CH:62]=[CH:63]/[CH3:64])[CH2:61][C@@H:16]12)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[Si:65]([O:72][C@@H:73]1[N:79]([C:80]([O:82][CH2:83][CH:84]=[CH2:85])=[O:81])[C:78]2[CH:86]=[C:87]([O:92][CH2:93][CH2:94][CH2:95]I)[C:88]([O:90][CH3:91])=[CH:89][C:77]=2[C:76](=[O:97])[N:75]2[CH:98]=[C:99](/[CH:101]=[CH:102]/[CH3:103])[CH2:100][C@@H:74]12)([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:67])[CH3:66]>CC(C)=O>[CH2:46]([O:45][C:43]([NH:42][C@H:38]([CH:39]([CH3:41])[CH3:40])[C:37]([NH:36][C@H:34]([CH3:35])[C:33]([NH:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][O:24][C:22]([N:21]2[C:20]3[CH:51]=[C:52]([O:57][CH2:95][CH2:94][CH2:93][O:92][C:87]4[C:88]([O:90][CH3:91])=[CH:89][C:77]5[C:76](=[O:97])[N:75]6[CH:98]=[C:99](/[CH:101]=[CH:102]/[CH3:103])[CH2:100][C@H:74]6[C@H:73]([O:72][Si:65]([C:68]([CH3:71])([CH3:69])[CH3:70])([CH3:67])[CH3:66])[N:79]([C:80]([O:82][CH2:83][CH:84]=[CH2:85])=[O:81])[C:78]=5[CH:86]=4)[C:53]([O:55][CH3:56])=[CH:54][C:19]=3[C:18](=[O:58])[N:17]3[CH:59]=[C:60](/[CH:62]=[CH:63]/[CH3:64])[CH2:61][C@H:16]3[C@@H:15]2[O:14][Si:7]([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:8])[CH3:9])=[O:23])=[CH:31][CH:30]=1)=[O:50])=[O:49])=[O:44])[CH:47]=[CH2:48]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 86717768HCID 86717768、化合物HCID 86717769(11 S,11aS)-4-((S)-2-((S)-2-(allyloxycarbonylamino)-3-methylbutanamido)propanamido)benzyl 11-(tert-butyldimethylsilyloxy)-8-hydroxy-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-11,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate

生成物 1

HCID 86717771
prop-2-enyl (6S,6aS)-3-[3-[[(6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-5-[[4-[[(2R)-2-[[(2R)-3-methyl-2-(prop-2-enoxycarbonylamino)butanoyl]amino]propanoyl]amino]phenyl]methoxycarbonyl]-11-oxo-8-[(E)-prop-1-enyl]-6a,7-dihydro-6H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-6-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-11-oxo-8-[(E)-prop-1-enyl]-6a,7-dihydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carboxylate
収率 35%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
75 °C

実験手順

Potassium carbonate (0.030 g, 0.21 mmol, 1.0 eq) was added to a solution of the phenol 18 (0.175 g, 0.21 mmol, 1.0 eq) and the iodo linker 49 (0.214 g, 0.32 mmol, 1.5 eq) in acetone (10 mL). The reaction mixture was heated under a nitrogen atmosphere at 75° C. in a sealed flask for 17 hours. The reaction mixture was concentrated to dryness under reduced pressure and purified by flash chromatography (silica gel, 2/98 v/v methanol/DCM to 5/95 v/v methanol/DCM) to afford the product as a pale yellow solid (0.100 g, 35%). LC/MS (4.293 min (ES+)), m/z: 1359.13 [M]+.

後処理

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. custompurified by flash chromatography (silica gel, 2/98 v/v methanol/DCM to 5/95 v/v methanol/DCM)

出典と根拠

ORDレコード
ord-760be87df7314406976ddc5764fd7fad
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102704B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート