Water → 5-[4-(4-(2-(2-t-Butoxycarbonylaminopropanamido}2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione

HRID 2111878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111878
Cl.[NH2:2][CH:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:23]=[CH:22][C:13]([CH2:14][CH:15]3[S:19][C:18](=[O:20])[NH:17][C:16]3=[O:21])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.[C:30]([O:34][C:35]([NH:37][CH:38]([CH3:42])[C:39](O)=[O:40])=[O:36])([CH3:33])([CH3:32])[CH3:31].C1(N=C=NC2CCCCC2)CCCCC1.O>O1CCCC1.C(OCC)(=O)C>[C:30]([O:34][C:35]([NH:37][CH:38]([CH3:42])[C:39]([NH:2][CH:3]([C:26]([O:28][CH3:29])=[O:27])[CH2:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[CH:23]=[CH:22][C:13]([CH2:14][CH:15]3[S:19][C:18](=[O:20])[NH:17][C:16]3=[O:21])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)=[O:40])=[O:36])([CH3:33])([CH3:32])[CH3:31]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 2684712-N-Boc-aminopropionic acidHCID 219896812-Amino-3-[4-[4-[(2,4-dioxo-5-thiazolidinyl)methyl]phenoxy]phenyl]propanoic acid methyl ester hydrochloride

Produkt 1

HCID 219896705-[4-(4-(2-(2-t-Butoxycarbonylaminopropanamido}2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dioneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione hydrochloride (2.3 g, 5.27 mmol) and 2-t-butoxycarbonylaminopropionic acid (0.997 g, 5.27 mmol) in tetrahydrofuran (20 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (1.086 g, 5.27 mmol) was added to this solution and stirring was continued for 1.5 h at ambient temperature. Water (200 ml) was added to the reaction mixture, stirred for 15 minutes, ethyl acetate (250 ml) was added and stirring was continued for another 15 minutes. The organic layer was separated and washed with water (100 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, which was purified by column chromatography (0.7 g, yield 23%).

Aufarbeitung

  1. stirringstirred for 15 minutes
  2. stirringstirring
  3. waitwas continued for another 15 minutes
  4. customThe organic layer was separated
  5. washwashed with water (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6cc18b903f347248b244f49c1ba9289
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521466B2

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