Hydrochloric Acid → methyl 4-[(2R)-2-({[(2R)-2-(6-amino-3-pyridinyl)-2-hydroxyethyl]amino}-methyl)-3,4-dihydro-2H-chromen-6-yl]benzoate

反応式

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:39])[CH2:9][N:10]([CH2:18][C@H:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29]4[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=4)[CH:25]=3)[O:20]2)C(OC(C)(C)C)=O)=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([OH:39])[CH2:9][NH:10][CH2:18][C@H:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29]4[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=4)[CH:25]=3)[O:20]2)=[CH:4][CH:3]=1

参加物

反応物 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 59118207Methyl 4-((2R)-2-{[[(2R)-2-(6-amino-3-pyridinyl)-2-hydroxyethyl](tert-butoxycarbonyl)amino]methyl}-3,4-dihydro-2H-chromen-6-yl)benzoate

生成物 1

HCID 59118232methyl 4-[(2R)-2-({[(2R)-2-(6-amino-3-pyridinyl)-2-hydroxyethyl]amino}-methyl)-3,4-dihydro-2H-chromen-6-yl]benzoate収率 62%

実験手順

Methyl 4-((2R)-2-{[[(2R)-2-(6-amino-3-pyridinyl)-2-hydroxyethyl](tert-butoxycarbonyl)-amino]methyl}-3,4-dihydro-2H-chromen-6-yl)benzoate (Example 377, 80 mg, 0.15 mmol) was added to 4 M hydrochloric acid in dioxane (3 mL, 12 mmol). The solution was stirred at room temperature for 18 hours and then concentrated in vacuo. The residue was purified by prep. HPLC, afforded 40 mg (62%) of the desired product. The product had: 1H NMR (CD3ODδ): 8.04 (d, J=8.1 Hz, 2 H), 7.89-8.03 (m, 2 H), 7.68 (d, J=7.8 Hz, 2 H), 7.42-7.49 (m, 2 H), 6.95-7.07 (m, 2 H), 5.02-5.10 (m, 1 H), 4.24-4.52 (m, 1 H), 3.91 (s, 3 H), 3.20-3.52 (m, 4 H), 2.81-3.04 (m, 2 H), 2.11-2.24 (m, 1 H), 1.74-1.92 (m, 1 H); mass spectroscopy gave m/z=434.2 [M+H]+ (calc'd exact mass for C25H27N3O4=433.2).