Formate → HCID 178425605, Verbindung

HRID 495042

Reaktionsgleichung

Reaktionsgleichung von HRID 495042
[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[NH:8][C:9]1[C:13](OCC)=[N:12][S:11](=[O:18])(=[O:17])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[CH3:31][C:32]1[CH:33]=[C:34]([NH:38][C:39]([NH:41][CH2:42][CH2:43][NH2:44])=[O:40])[CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[NH:8][C:9]1[C:13]([NH:44][CH2:43][CH2:42][NH:41][C:39]([NH:38][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([CH3:31])[CH:33]=2)=[O:40])=[N:12][S:11](=[O:17])(=[O:18])[N:10]=1)([CH3:3])([CH3:4])[CH3:2]

Komponenten

6

Edukt 4

HCID 283FormateHCID 8471TriethylamineHCID 221388592-(3-Methylphenylaminocarbonylamino)eth-1-ylamineHCID 178467516HCID 178467516, Verbindung

Produkt 1

HCID 178425605HCID 178425605, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of N-(4-ethoxy-1,1-dioxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester from Step A (150 mg, 0.38 mmol) and the formate salt of 2-(3-methylphenylaminocarbonylamino)eth-1-ylamine from Step B (210 mg, 0.89 mmol) in ethanol (10 mL) was added triethylamine (133 mg, 1.44 mmol). The reaction was stirred at room temperature overnight. Solvent was removed under reduced pressure and the residue purified by flash column chromatography (silica, 5% MeOH in EtOAc) to give N-[4-(2-(3-methylphenylamino-carbonylamino)eth-1-ylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]-L-tyrosine tert-butyl ester (130 mg, 91%). MS (+ESI, m/e) 545 (M+H)+.

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by flash column chromatography (silica, 5% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-2384c864ec2d49e68936eff3c5de6883
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538215B2

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