Hydrochloric Acid → (S)-methyl 2-amino-6-(3-oxocyclobutanecarboxamido)hexanoate
Reaktionsgleichung
C(OC([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)=[O:20])[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@@H:9]([CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([CH:21]1[CH2:24][C:23](=[O:25])[CH2:22]1)=[O:20])[C:10]([O:12][CH3:13])=[O:11]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
(S)-methyl 2-(tert-butoxycarbonylamino)-6-(3-oxocyclobutanecarboxamido)hexanoate (0.501 g) was treated with 20 mL 4M HCl in 1,4-dioxane at ambient temperature for 20 minutes and the solvent was removed under reduced pressure. The resulting viscous oil was taken up in 10 mL CH3CN, and seeded with small amount of crystals of the title compound prepared in a smaller scale. The resulting crystals were collected by vacuum filtration, washed with CH3CN, and dried under reduced pressure, affording (S)-methyl 2-amino-6-(3-oxocyclobutanecarboxamido)hexanoate (TU3205-016) as color less solid. MS (ESI+): calcd. 257.15. found 257.20 (MH+). H-NMR (400 MHz, DMSO-d6):1.267 (1H, m), 1.419 (3H, m), 1.753 (2H, m), 3.114 (7H, m), 3.752 (3H, m), 4.023 (1H, t, J=6.4 Hz), 8.169 (1H, t, J=5.5 Hz), 8.365 (3H, br.s). C-NMR (100 MHz, DMSO-d6): 21.499, 27.160, 28.390, 29.548, 38.067, 50.858, 51.721, 52.727, 169.949, 173.034, 205.586.