1,2-Dichloroethane → 2,5-Dioxopyrrolidin-1-yl 18-((4-(3,5-dioxohexyl)phenyl)amino)-14,18-dioxo-4,7,10-trioxa-13-azaoctadecan-1-oate

HRID 1402664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402664
C([O:5][C:6](=[O:41])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:40])[CH2:20][CH2:21][CH2:22][C:23](=[O:39])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33](=[O:38])[CH2:34][C:35](=[O:37])[CH3:36])=[CH:27][CH:26]=1)(C)(C)C.CCN(C(C)C)C(C)C.O[N:52]1[C:56](=[O:57])[CH2:55][CH2:54][C:53]1=[O:58].C(Cl)CCl>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[O:58]=[C:53]1[CH2:54][CH2:55][C:56](=[O:57])[N:52]1[O:5][C:6](=[O:41])[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][NH:18][C:19](=[O:40])[CH2:20][CH2:21][CH2:22][C:23](=[O:39])[NH:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][C:33](=[O:38])[CH2:34][C:35](=[O:37])[CH3:36])=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 80170N-HydroxysuccinimideHCID 81531DiisopropylethylamineHCID 670685163-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

Produkt 1

HCID 114563222,5-Dioxopyrrolidin-1-yl 18-((4-(3,5-dioxohexyl)phenyl)amino)-14,18-dioxo-4,7,10-trioxa-13-azaoctadecan-1-oate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

3-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (400 mg, 0.692 mmol) was dissolved in TFA/CH2Cl2 (1:1, 3 mL) and the mixture stirred overnight. The solvent was removed to give an oil as the acid intermediate. This oil was dissolved in CH2Cl2 (4 mL) containing DIEA (569 L, 3.09 mmol), N-hydroxysuccinimide (119 mg, 1.03 mmol) and EDC (197 mg, 1.0 mmol) and the mixture stirred over the night. The solvent was removed and the residual oil was purified using column chromatography EtOAc/MeOH (95:5) to give an oil as the title compound, (M+1)=620.

Aufarbeitung

  1. customThe solvent was removed
  2. customto give an oil as the acid intermediate
  3. stirringthe mixture stirred over the night
  4. customThe solvent was removed
  5. customthe residual oil was purified

Quellen und Nachweise

ORD-Eintrag
ord-66095fd072de4a0ba4ad2f68b3743a11
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912148B2

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