2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → 1-(2-iodoacetamido)-N-((S)-1-((S)-1-((E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylamino)-1-oxopropan-2-ylamino)-3-methyl-1-oxobutan-2-yl)-3,6,9,12-tetraoxapentadecan-15-amide

HRID 1057085ノート

反応式

HRID 1057085 の反応式
C(OC1C=CC2C(=CC=CC=2)N1C(OCC)=O)C.[NH2:19][C@@H:20]([CH:74]([CH3:76])[CH3:75])[C:21]([NH:23][C@@H:24]([CH3:73])[C:25]([NH:27][CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH2:32][C@H:33]2[CH:39]=[N:38][C:37]3[CH:40]=[C:41]([O:46][CH2:47][CH2:48][CH2:49][O:50][C:51]4[C:52]([O:69][CH3:70])=[CH:53][C:54]5[C:60](=[O:61])[N:59]6[CH:62]=[C:63](/[CH:65]=[CH:66]/[CH3:67])[CH2:64][C@H:58]6[CH:57]=[N:56][C:55]=5[CH:68]=4)[C:42]([O:44][CH3:45])=[CH:43][C:36]=3[C:35](=[O:71])[N:34]2[CH:72]=1)=[O:26])=[O:22].[I:77][CH2:78][C:79](=[O:98])[NH:80][CH2:81][CH2:82][O:83][CH2:84][CH2:85][O:86][CH2:87][CH2:88][O:89][CH2:90][CH2:91][O:92][CH2:93][CH2:94][C:95](O)=[O:96]>ClCCl>[I:77][CH2:78][C:79]([NH:80][CH2:81][CH2:82][O:83][CH2:84][CH2:85][O:86][CH2:87][CH2:88][O:89][CH2:90][CH2:91][O:92][CH2:93][CH2:94][C:95]([NH:19][C@@H:20]([CH:74]([CH3:76])[CH3:75])[C:21]([NH:23][C@@H:24]([CH3:73])[C:25]([NH:27][CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH2:32][C@H:33]2[CH:39]=[N:38][C:37]3[CH:40]=[C:41]([O:46][CH2:47][CH2:48][CH2:49][O:50][C:51]4[C:52]([O:69][CH3:70])=[CH:53][C:54]5[C:60](=[O:61])[N:59]6[CH:62]=[C:63](/[CH:65]=[CH:66]/[CH3:67])[CH2:64][C@H:58]6[CH:57]=[N:56][C:55]=5[CH:68]=4)[C:42]([O:44][CH3:45])=[CH:43][C:36]=3[C:35](=[O:71])[N:34]2[CH:72]=1)=[O:26])=[O:22])=[O:96])=[O:98]

参加物

5

反応物 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 872435891-Iodo-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oic acidHCID 90408320(S)-2-amino-N-((S)-1-((E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylamino)-1-oxopropan-2-yl)-3-methylbutanamide

生成物 1

HCID 904080301-(2-iodoacetamido)-N-((S)-1-((S)-1-((E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-5-oxo-2-((E)-prop-1-enyl)-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5-oxo-5,11a-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylamino)-1-oxopropan-2-ylamino)-3-methyl-1-oxobutan-2-yl)-3,6,9,12-tetraoxapentadecan-15-amide収率 29%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (0.007 g, 0.0290 mmol, 1.0 eq) was added to a solution of amine 20c (assumed 100%, 0.023 g, 0.0290 mmol, 1.0 eq) and 1-iodo-2-oxo-6,9,12,15-tetraoxa-3-azaoctadecan-18-oic acid (I5)(0.0126 g, 0.0290 mmol, 1.0 eq) in dry dichloromethane (2 mL). The reaction mixture was stirred for 18 hours, then diluted with DCM (6 mL) and washed with water (2×10 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was subjected to flash chromatography (silica gel; 40:1 v/v DCM/MeOH to 5:1 v/v DCM/MeOH) to afford the product as a pale yellow oil (0.0043 g, 29%). LC/MS (2.380 min (ES+)), m/z: 605.0 ½[M+2H]+.

後処理

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-373c80d943914826bc966ae19280a5cd
出典データセット
uspto-grants-2016_07
特許番号
US09399073B2

反応ノート

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