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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2S)-1-[[(E)-3-[(6aS)-3-[3-[[(6aS)-2-methoxy-6,11-dioxo-8-[(E)-prop-1-enyl]-5-(2-trimethylsilylethoxymethyl)-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-2-methoxy-6,11-dioxo-5-(2-trimethylsilylethoxymethyl)-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enyl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate

HRID 1057079
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Reaktionsgleichung

Reaktionsgleichung von HRID 1057079
Cl.C(N=C=NCCCN(C)C)C.[NH2:13][CH2:14]/[CH:15]=[CH:16]/[C:17]1[CH2:18][C@H:19]2[C:25](=[O:26])[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:23]3[CH:35]=[C:36]([O:41][CH2:42][CH2:43][CH2:44][O:45][C:46]4[C:47]([O:73][CH3:74])=[CH:48][C:49]5[C:55](=[O:56])[N:54]6[CH:57]=[C:58](/[CH:60]=[CH:61]/[CH3:62])[CH2:59][C@H:53]6[C:52](=[O:63])[N:51]([CH2:64][O:65][CH2:66][CH2:67][Si:68]([CH3:71])([CH3:70])[CH3:69])[C:50]=5[CH:72]=4)[C:37]([O:39][CH3:40])=[CH:38][C:22]=3[C:21](=[O:75])[N:20]2[CH:76]=1.[CH:77]1[C:89]2[CH:88]([CH2:90][O:91][C:92]([NH:94][C@@H:95]([CH:104]([CH3:106])[CH3:105])[C:96]([NH:98][C@@H:99]([CH3:103])[C:100](O)=[O:101])=[O:97])=[O:93])[C:87]3[C:82](=[CH:83][CH:84]=[CH:85][CH:86]=3)[C:81]=2[CH:80]=[CH:79][CH:78]=1>ClCCl>[CH3:40][O:39][C:37]1[C:36]([O:41][CH2:42][CH2:43][CH2:44][O:45][C:46]2[C:47]([O:73][CH3:74])=[CH:48][C:49]3[C:55](=[O:56])[N:54]4[CH:57]=[C:58](/[CH:60]=[CH:61]/[CH3:62])[CH2:59][C@H:53]4[C:52](=[O:63])[N:51]([CH2:64][O:65][CH2:66][CH2:67][Si:68]([CH3:71])([CH3:70])[CH3:69])[C:50]=3[CH:72]=2)=[CH:35][C:23]2[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25](=[O:26])[C@@H:19]3[CH2:18][C:17](/[CH:16]=[CH:15]/[CH2:14][NH:13][C:100](=[O:101])[C@@H:99]([NH:98][C:96](=[O:97])[C@@H:95]([NH:94][C:92](=[O:93])[O:91][CH2:90][CH:88]4[C:89]5[CH:77]=[CH:78][CH:79]=[CH:80][C:81]=5[C:82]5[C:87]4=[CH:86][CH:85]=[CH:84][CH:83]=5)[CH:104]([CH3:106])[CH3:105])[CH3:103])=[CH:76][N:20]3[C:21](=[O:75])[C:22]=2[CH:38]=1
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Komponenten

5

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11165770Fmoc-Val-Ala-OHHCID 90407563(S)-2-((E)-3-aminoprop-1-enyl)-7-methoxy-8-(3-((S)-7-methoxy-5,11-dioxo-2-((E)-prop-1-enyl)-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

Produkt 1

HCID 131736460
9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2S)-1-[[(E)-3-[(6aS)-3-[3-[[(6aS)-2-methoxy-6,11-dioxo-8-[(E)-prop-1-enyl]-5-(2-trimethylsilylethoxymethyl)-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-2-methoxy-6,11-dioxo-5-(2-trimethylsilylethoxymethyl)-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-8-yl]prop-2-enyl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate
Ausbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.0641 g, 0.334 mmol, 1.0 eq.) was added to a solution of allylamine 17c (assumed 100% yield, 0.306 g, 0.334 mmol, 1.0 eq.) and HO-Ala-Val-Fmoc 12 (0.1367 g, 0.334 mmol, 1.0 eq.) in dry dichloromethane (18 mL). The reaction mixture was stirred for 95 minutes at room temperature when the reaction mixture was diluted with dichloromethane (30 mL) and washed sequentially with water (30 mL) and brine (30 mL). The organic layer was dried over MgSO4 filtered and excess dichloromethane removed under reduced pressure. The resulting residue was purified by flash chromatography (silica gel; 100:1 v/v DCM/MeOH to 40:1 v/v DCM/MeOH) to afford the product as a yellow solid (0.220 g, 50%). LC/MS (3.804 min (ES+)), m/z: 1307.37 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.76 (d, 2H, J=7.6 Hz), 7.57 (m, 2H), 7.39 (t, 2H, J=7.6 Hz), 7.34 (d, 2H, J=3.2 Hz), 7.31 (m, 3H), 7.26 (m, 1H), 6.93 (s, 1H), 6.85 (m, 1H), 6.36 (m, 2H), 6.24 (d, 1H, J=14.7 Hz), 5.68 (m, 1H), 5.58 (m, 1H), 5.49 (m, 2H), 4.72 (m, 2H), 4.83 (m, 4H), 4.39 (m, 1H), 4.27 (m, 4H), 4.22 (t, 1H, J=6.9 Hz), 3.98 (m, 3H), 3.89 (m, 8H), 3.75 (m, 2H), 3.65 (m, 4H), 2.85 (m, 2H), 2.43 (m, 2H), 2.14 (m, 1H), 1.82 (dd, 3H, J=5.8, 0.8 Hz), 1.40 (d, 3H, J=6.9 Hz), 0.99-0.92 (m, 10H), 0.01 (s, 9H), 0.00 (s, 9H).

Aufarbeitung

  1. washwashed sequentially with water (30 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customexcess dichloromethane removed under reduced pressure
  5. customThe resulting residue was purified by flash chromatography (silica gel; 100:1 v/v DCM/MeOH to 40:1 v/v DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-2f38c00460bd45f3afe4c1854ca3fe69
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09399073B2

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