Dimethylamine → HCID 67338116、化合物

HRID 1670118ノート

反応式

HRID 1670118 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:19]=2[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:10]=1)[C:5](O)=[O:6].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:49]1[CH2:53]CC[CH2:50]1.CNC.C1COCC1.CCN(C(C)C)C(C)C>ClCCl.O>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][O:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:9]2[CH:8]=[C:4]([C:5](=[O:6])[N:49]([CH3:53])[CH3:50])[CH:3]=[C:2]([Br:1])[CH:10]=2)[C:19]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:32]

参加物

8

反応物 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 67340836HCID 67340836、化合物

生成物 1

HCID 67338116HCID 67338116、化合物収率 90%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 3-bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic acid (808 mg, 1.33 mmol), bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP) (745 mg, 1.6 mmol) in dichloromethane (15 mL) were added dimethylamine in THF (800 μL, 1.6 mmol, 2 M solution) and DIPEA (463 μL, 2.66 mmol) at room temperature. The resulting clear solution was stirred for 36 h. Then, the reaction mixture was diluted with water (100 mL) and dichloromethane (50 mL). The two layers were separated and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic extracts were washed with brine solution (200 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and concentration of the filtrate in vacuo gave the crude product which was purified by using an ISCO™ (40 g) column chromatography eluting with 40-60% ethyl acetate in hexanes to afford 4-{3-[6-(3-bromo-5-dimethylcarbamoyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (757 mg, 90%) as a colorless oil

後処理

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  3. washThe combined organic extracts were washed with brine solution (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration of the drying agent and concentration of the filtrate in vacuo
  6. customgave the crude product which
  7. customwas purified
  8. washeluting with 40-60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-70e1d38d6f754ba491611299ab959475
出典データセット
uspto-grants-2011_08
特許番号
US07989454B2

反応ノート

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