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

HRID 1050447ノート

反応式

HRID 1050447 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-853d1aba25534b2f8b2ba8abfd569bbb
出典データセット
uspto-grants-2016_07
特許番号
US09382234B2

反応ノート

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