Piperidine → (S)-2-((E)-3-aminoprop-1-enyl)-7-methoxy-8-(3-((S)-7-methoxy-2-methyl-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-10-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11(10H,11aH)-dione

HRID 1057075ノート

反応式

HRID 1057075 の反応式
N1CCCCC1.[CH3:7][O:8][C:9]1[C:53]([O:54][CH2:55][CH2:56][CH2:57][O:58][C:59]2[C:60]([O:84][CH3:85])=[CH:61][C:62]3[C:68](=[O:69])[N:67]4[CH:70]=[C:71]([CH3:73])[CH2:72][C@H:66]4[C:65](=[O:74])[N:64]([CH2:75][O:76][CH2:77][CH2:78][Si:79]([CH3:82])([CH3:81])[CH3:80])[C:63]=3[CH:83]=2)=[CH:52][C:12]2[N:13]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[C:14](=[O:43])[C@@H:15]3[CH2:21][C:20](/[CH:22]=[CH:23]/[CH2:24][NH:25]C(=O)OCC4C5C=CC=CC=5C5C4=CC=CC=5)=[CH:19][N:16]3[C:17](=[O:18])[C:11]=2[CH:10]=1>CN(C=O)C>[NH2:25][CH2:24]/[CH:23]=[CH:22]/[C:20]1[CH2:21][C@H:15]2[C:14](=[O:43])[N:13]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:50])([CH3:49])[CH3:51])[C:12]3[CH:52]=[C:53]([O:54][CH2:55][CH2:56][CH2:57][O:58][C:59]4[C:60]([O:84][CH3:85])=[CH:61][C:62]5[C:68](=[O:69])[N:67]6[CH:70]=[C:71]([CH3:73])[CH2:72][C@H:66]6[C:65](=[O:74])[N:64]([CH2:75][O:76][CH2:77][CH2:78][Si:79]([CH3:80])([CH3:82])[CH3:81])[C:63]=5[CH:83]=4)[C:9]([O:8][CH3:7])=[CH:10][C:11]=3[C:17](=[O:18])[N:16]2[CH:19]=1

参加物

4

反応物 2

HCID 8082PiperidineHCID 131736458(9H-fluoren-9-yl)methyl(E)-3-((S)-7-methoxy-8-(3-((S)-7-methoxy-2-methyl-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-2-yl)allylcarbamate

生成物 1

HCID 90407865(S)-2-((E)-3-aminoprop-1-enyl)-7-methoxy-8-(3-((S)-7-methoxy-2-methyl-5,11-dioxo-10-((2-(trimethylsilyl)ethoxy)methyl)-5,10,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yloxy)propoxy)-10-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11(10H,11aH)-dione収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Piperidine (0.133 mL, 1.35 mmol, 12 eq.) was added to a stirred solution of Fmoc amine 14a (0.125 g, 0.112 mmol, 1.0 eq.) in DMF (1.8 ml). After stirring at room temperature for 30 minutes, LCMS analysis indicated consumption of starting material and the reaction mixture was diluted with DCM (200 mL) and washed with water (3×200 mL). The organic layer was dried over MgSO4, filtered and concentrated to dryness to afford the crude product which did not undergo further purification (0.100 g, assumed 100% yield). This material was used without further characterisation.

後処理

  1. customconsumption of starting material
  2. additionthe reaction mixture was diluted with DCM (200 mL)
  3. washwashed with water (3×200 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-d338d3ef76234051a0c4bec681d17ffe
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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