Triethylamine → 4-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester

HRID 1755100ノート

反応式

HRID 1755100 の反応式
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20])=[C:13]([CH3:23])[CH:12]=1.[CH2:25]([O:29][C:30]1[CH:31]=[C:32]([C:40]2[NH:44][C:43](=[O:45])[C:42]3([CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[N:41]=2)[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:26][CH:27]=[CH2:28]>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19]([N:48]2[CH2:49][CH2:50][C:42]3([N:41]=[C:40]([C:32]4[CH:33]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:35]=[C:30]([O:29][CH2:25][CH2:26][CH:27]=[CH2:28])[CH:31]=4)[NH:44][C:43]3=[O:45])[CH2:46][CH2:47]2)(=[O:21])=[O:20])=[C:13]([CH3:23])[CH:12]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 668171362-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-oneHCID 866727954-(2-Chlorosulfonyl-ethyl)-3-methyl-benzoic acid methyl ester

生成物 1

HCID 668187074-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester収率 94.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (1.27 ml, 9.11 mmol) and 4-(2-chlorosulfonyl-ethyl)-3-methyl-benzoic acid methyl ester (1.01 g, 3.65 mmol) were added to a solution of 2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (1.40 g, 3.83 mmol) in methylene chloride (35 ml) at 0° C. The mixture was stirred at room temperature for two hours, and then quenched with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester (2.10 g). This compound was used in the next reaction without further purification.

後処理

  1. customquenched with a saturated aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7755b2209c6c48eabc92be2825724f02
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

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