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 1057085노트

반응식

HRID 1057085 반응식
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]

참가 물질

5

반응물 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

생성물 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-amide수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-373c80d943914826bc966ae19280a5cd
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399073B2

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