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Synthesis and activity of (R)-(−)-m-trimethylacetoxy-α-[(methylamino)methyl]benzyl alcohol hydrochloride: A prodrug form of (R)-(−)-phenylephrine

✍ Scribed by Sun-Shine Yuan; Nicolae Bodor

Publisher
John Wiley and Sons
Year
1976
Tongue
English
Weight
355 KB
Volume
65
Category
Article
ISSN
0022-3549

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✦ Synopsis

Amino-5-carboxypentyl)-6,7-dihydro-2,10-bis (trifluoromethyl)-5H-dibenz(c,e]azepine Dihydrobromide (IIIe)-a-Carbobenzoxy-L-lysine (1.29 g, 0.004 mole), 1.52 g (0.004 mole) of V, and sodium hydrosulfite (5.3 g, 0.03 mole) were allowed to react by the procedure of Hawthorne et al. (6). The reaction mixture was filtered to give a white solid, which was recrystallized from acetone to give 0.5 g (I%), mp 199-201'. This solid was treated with 5 ml of hydrobromic acid-acetic acid (30-32%) at room temperature for 1 hr. Upon addition of ether, the product precipitated and was collected. Recrystallization from ethanohther gave 0.43 g (93%) of white powder, mp 230-232'; NMR 6 7.4-8.0 (m), 5.0-5.5 (m), 3.4-4.2 (m), 2.8-3.2 (m), and 1.0-2.1 (m) ppm.

Anal.-Calc. for C ~~H ~~F ~N ~O Y ~H B T : C, 42.47; H, 3.89; N, 4.50.

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