Piperidine → Cypate Lys

HRID 2262450

Reaktionsgleichung

Reaktionsgleichung von HRID 2262450
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].N1CCCCC1.[CH3:34][C:35]1([CH3:80])[C:47](/[CH:48]=[CH:49]/[CH:50]=[CH:51]/[CH:52]=[CH:53]/[CH:54]=[C:55]2\[C:56]([CH3:74])([CH3:73])[C:57]3[C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][C:63]=4[CH:64]=[CH:65][C:66]=3[N:67]\2[CH2:68][CH2:69][C:70]([OH:72])=[O:71])=[N+:46]([CH2:75][CH2:76][C:77]([OH:79])=[O:78])[C:45]2[CH:44]=[CH:43][C:42]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:36]1=2.[Br-:81].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C>[CH3:34][C:35]1([CH3:80])[C:47](/[CH:48]=[CH:49]/[CH:50]=[CH:51]/[CH:52]=[CH:53]/[CH:54]=[C:55]2\[C:56]([CH3:73])([CH3:74])[C:57]3[C:58]4[CH:59]=[CH:60][CH:61]=[CH:62][C:63]=4[CH:64]=[CH:65][C:66]=3[N:67]\2[CH2:68][CH2:69][C:70]([OH:72])=[O:71])=[N+:46]([CH2:75][CH2:76][C:77]([OH:79])=[O:78])[C:45]2[CH:44]=[CH:43][C:42]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:36]1=2.[Br-:81].[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Komponenten

7

Edukt 5

HCID 8082PiperidineHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7010557(2S)-6-amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acidHCID 10963571Cypate

Produkt 1

HCID 137227855Cypate Lys

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Fmoc-Lys was attached to Rink amide resin (60 mg, 0.0366 mmol) and the Fmoc was deprotected by piperidine in DMF (20%). A solution of Cypate(129 mg, 5 equiv), HOBT(24.7 mg), and DIC (11.5 mg, 2.5 equiv) in DMF (3 mL) was added into the resin and swirled overnight. After filtered, the resin was washed with DMF and DCM, cleaved with TFA/H2O (95:5) for 3 h, filtered, concentrated, and dried. The crude product was dissolved in 20 mL DCM and added dropwise into a stirred solution of PyBOP (38 mg), HOBT (9.9 mg), and DIEA (18.9 mg) in DCM/DMF(195:5, 200 mL) and the resulting mixture was stirred overnight, concentrated, and purified by HPLC to afforded 1.5 mg of the desired product.

Aufarbeitung

  1. filtrationAfter filtered
  2. washthe resin was washed with DMF and DCM
  3. waitcleaved with TFA/H2O (95:5) for 3 h
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried
  7. dissolutionThe crude product was dissolved in 20 mL DCM
  8. additionadded dropwise into a stirred solution of PyBOP (38 mg), HOBT (9.9 mg), and DIEA (18.9 mg) in DCM/DMF(195:5, 200 mL)
  9. concentrationconcentrated
  10. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-aa76334da9fb4cd3a3d7ce853bf23189
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07850946B2

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