Hydrochloric Acid → N-((5S)-5-amino-6-hydroxy-7-oxo-7-{[(1R)-1-phenylethyl]amino}heptyl)-4-morpholinecarboxamide hydrochloride

HRID 1180747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180747
[OH:1][CH:2]([C@@H:14]([NH:28]C(=O)OC(C)(C)C)[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].[ClH:36]>C(OCC)(=O)C>[ClH:36].[NH2:28][C@H:14]([CH:2]([OH:1])[C:3](=[O:13])[NH:4][C@@H:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:6])[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)=[O:21]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 58979673tert-butyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate

Produkt 1

HCID 69236903N-((5S)-5-amino-6-hydroxy-7-oxo-7-{[(1R)-1-phenylethyl]amino}heptyl)-4-morpholinecarboxamide hydrochlorideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 830 mg (1.7 mmol) of tert-butyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)-5-[(4-morpholinylcarbonyl)amino]pentylcarbamate in 100 mL of ethyl acetate was bubbled with hydrogen chloride gas for 5 min and the reaction allowed to stir for 10 min before being conentrated under reduced pressure to afford 720 mg (>99%) of N-((5S)-5-amino-6-hydroxy-7-oxo-7-{[(1R)-1-phenylethyl]amino}heptyl)-4-morpholinecarboxamide hydrochloride. 1H NMR (300 MHz, DMSO-d6) δ 8.46 (d, J=8 Hz, 1H), 7.97 (m, 1H), 7.82 (m, 2H), 7.31 (m, 4H), 7.22 (m, 1H), 6.50 (m, 1H), 4.94 (qnt, 1H), 3.83 under water peak (m, 2H), 3.50 (t, J=5 Hz, 4H), 3.22 (t, J=5 Hz, 4H), 2.98 (m, 2H), 1.20-1.61 (m, 9H). ES-LCMS m/z 393 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-73e59f9a5c9e4bab9c6262cf5f497c87
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282512B2

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