ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sodium Bicarbonate → t-Butyl 4-{4-[({2-[(t-butoxycarbonyl)amino]phenyl}amino)carbonyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate

HRID 888045
ノート
印刷プレビュー

反応式

HRID 888045 の反応式
C(=O)([O-])O.[Na+].FC(F)(F)S(O[C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=1)(=O)=O.[C:27]([O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42](=[O:58])[C:43]1[CH:48]=[CH:47][C:46](B2OC(C)(C)C(C)(C)O2)=[CH:45][CH:44]=1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:27]([O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42]([C:43]1[CH:48]=[CH:47][C:46]([C:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]=2)=[CH:45][CH:44]=1)=[O:58])=[O:33])([CH3:30])([CH3:28])[CH3:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

生成物 1

HCID 68407877t-Butyl 4-{4-[({2-[(t-butoxycarbonyl)amino]phenyl}amino)carbonyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate収率 74.3%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A saturated solution of sodium hydrogen carbonate (3 ml) was added to a stirred solution of t-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (Method 72, 200 mg, 0.60 mmol) in 1,2-dimethoxyethane (3 ml). N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13) (318 mg, 0.72 mmol) was added followed by tetrakis(triphenylphosphine) palladium (100 mg, 0.09 mmol) and the mixture stirred at 80° C. for 18 hours. The cooled mixture was partitioned between ethyl acetate and water. The organic phase was separated, then washed with water and dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by flash column chromatography (eluting with 0-15% methanol in dichloromethane) to give the title compound (220 mg, 74%); NMR Spectrum: (DMSO-d6) 1.42 (s, 9H), 1.43 (s, 9H), 2.48 (m, 2H), 3.55 (m, 2H), 4.02 (m, 2H), 6.31 (s, 1H), 7.17 (m, 2H), 7.52 (m, 2H), 7.58 (d, 2H), 7.92 (d, 2H), 8.62 (s, 1H), 9.79 (s, 1H); Mass Spectrum: M+H+ 494.

後処理

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by flash column chromatography (eluting with 0-15% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-9e249831663449c38213aca4e73a6e1d
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08247562B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート