Hydrochloric Acid → 3-((1-((Benzyloxy)carbonyl)piperidin-4-yl)oxy)-5-chloro-2-methylbenzoic acid

HRID 1050447Notizen

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C:26]([O:28]C)=[O:27])[C:5]([CH3:25])=[C:6]([CH:24]=1)[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH2:9]1.[OH-].[Na+].Cl>O1CCCC1.CO.O>[CH2:17]([O:16][C:14]([N:11]1[CH2:10][CH2:9][CH:8]([O:7][C:6]2[C:5]([CH3:25])=[C:4]([CH:3]=[C:2]([Cl:1])[CH:24]=2)[C:26]([OH:28])=[O:27])[CH2:13][CH2:12]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

To a solution of benzyl 4-(5-chloro-3-(methoxycarbonyl)-2-methylphenoxy)piperidine-1-carboxylate (0.68 g, 1.627 mmol) in tetrahydrofuran (5 mL) and methanol (15 mL) was added 3 N NaOH (2.71 mL, 8.14 mmol). The reaction mixture was stirred for 1 h, then heated at 45° C. for 3 h. The volatiles were removed in vacuo to give an aqueous residue, which was diluted with water (25 mL) and cooled (ice bath). The mixture was acidified to pH˜3-4 with 1 M HCl and stirred for 15 min. The solids were filtered, washed with water, and dried under high vacuum overnight to give 3-((1-((benzyloxy)carbonyl)piperidin-4-yl)oxy)-5-chloro-2-methylbenzoic acid (0.52 g, 1.223 mmol, 75% yield). 1H NMR δ 1.54-1.72 (m, 2H), 1.83-1.98 (m, 2H), 2.29 (s, 3H), 3.38 (br. s., 2H), 3.58-3.70 (m, 2H), 4.72 (tt, 1H), 5.09 (s, 2H), 7.24-7.46 (m, 7H), 13.28 (br. s., 1H). MS(ES) [M+H]+ 404.1.

Aufarbeitung

customThe volatiles were removed in vacuo
customto give an aqueous residue, which
temperaturecooled (ice bath)
stirringstirred for 15 min
filtrationThe solids were filtered
washwashed with water
customdried under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag: ord-853d1aba25534b2f8b2ba8abfd569bbb
Quelldatensatz: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09382234B2

Notizen zur Reaktion

Wird geladen…