Triethylamine → cis-6-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid

HRID 736706ノート

反応式

HRID 736706 の反応式
[NH2:1][C@H:2]1[CH2:7][CH:6]=[CH:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.Cl.[CH3:19][C:20]1[CH:29]=[C:28]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1>O1CCOCC1.O>[CH3:19][C:20]1[CH:29]=[C:28]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([S:38]([NH:1][C@@H:2]3[C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH:5]=[CH:6][CH2:7]3)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2724811cis-2-Amino-4-cyclohexene-1-carboxylic acidHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

生成物 1

HCID 68819512cis-6-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid収率 77.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 423.5 mg (3 mmol) of cis-2-amino-4-cyclohexene-1-carboxylic acid in 8 mL of dioxane and 8 mL of water was added 2.1 mL of triethylamine, followed by 1.13 g (3 mmol) of 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride in one portion as a solid. The solution was stirred at room temperature overnight. After removal of the volatile material, 10 mL of dichloromethane and 10 mL of water were added to the residue. The mixture was adjusted pH to 5 with 1N HCl solution. The solid was collected by filtration, washed with a small volume of water, followed by dichloromethane to provide 1.05 g of cis-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohex-3-ene-1-carboxylic acid in 77% yield. MS: 453.1 (M+H)+

後処理

  1. customAfter removal of the volatile material, 10 mL of dichloromethane and 10 mL of water
  2. additionwere added to the residue
  3. filtrationThe solid was collected by filtration
  4. washwashed with a small volume of water

出典と根拠

ORDレコード
ord-0d46003e51014df3803d3a83f145843a
出典データセット
uspto-grants-2009_09
特許番号
US07595327B2

反応ノート

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