Diisopropylethylamine → ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate

HRID 363147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363147
Cl.NC[C:4]1[CH:5]=[C:6]([OH:15])[C:7](=[CH:13][CH:14]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:16]([N:19](CC)C(C)C)(C)C.C1(=O)N(O[C:31](=[O:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])C(=O)CC1>CN(C)C=O.C(OCC)(=O)C>[C:41]([O:40][C:38]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][C:31]([NH:19][CH2:16][O:15][C:6]1[C:7](=[CH:13][CH:14]=[CH:4][CH:5]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:45])=[O:39])([CH3:42])([CH3:43])[CH3:44]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 5074016Boc-6-Ahx-OSuHCID 12794728Ethyl 4-aminomethylsalicylate hydrochloride

Produkt 1

HCID 53930957ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylateAusbeute 128,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 4-aminomethylsalicylate hydrochloride (0.52 g 1.28 mmoles) was suspended in anhydrous N,N-dimethylformamide (25 mL), and N,N-diisopropylethylamine (0.79 mL, 4.53 mmoles) was added, followed by N-tert-butoxycarbonyl-6-aminohexanoic acid succinimidyl ester (0.74 g, 2.26 mmoles). The mixture was stirred under dry nitrogen for 18 hours, during which time all solids dissolved. The reaction mixture was diluted with ethyl acetate (100 mL) and extracted with 1N aqueous hydrochloric acid (100 mL). The layers were separated, and the ethyl acetate solution was washed with water (100 mL) and saturated aqueous sodium chloride (500 mL). The ethyl acetate solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to afford an amorphous off-white solid. Finally, the solid was crystallized from ethyl acetate, filtered, and dried in vacuo to afford 0.67 g (73% yield) of ethyl (N-tert-butoxycarbonyl-6-aminohexanoyl)aminomethylsalicylate (m.p. 120°-121° C., open capillary, uncorrected).

Aufarbeitung

  1. dissolutiondissolved
  2. extractionextracted with 1N aqueous hydrochloric acid (100 mL)
  3. customThe layers were separated
  4. washthe ethyl acetate solution was washed with water (100 mL) and saturated aqueous sodium chloride (500 mL)
  5. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an amorphous off-white solid
  9. customFinally, the solid was crystallized from ethyl acetate
  10. filtrationfiltered
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-88158683d9cb4675bd62f95e3c2f4a5b
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872224

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