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

HRID 736706노트

반응식

HRID 736706 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-0d46003e51014df3803d3a83f145843a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595327B2

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