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

HRID 1050447노트

반응식

HRID 1050447 반응식
[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

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90278022Benzyl 4-(5-chloro-3-(methoxycarbonyl)-2-methylphenoxy)piperidine-1-carboxylate

생성물 1

HCID 902733993-((1-((Benzyloxy)carbonyl)piperidin-4-yl)oxy)-5-chloro-2-methylbenzoic acid수율 75.2%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-853d1aba25534b2f8b2ba8abfd569bbb
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382234B2

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