4-Hydroxybenzoic Acid → HCID 86638568、化合物

HRID 1807776ノート

反応式

HRID 1807776 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[F:11][C:12]([F:33])([F:32])[C:13]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:21][CH:20]=1)([OH:18])[C:14]([F:17])([F:16])[F:15].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[F:33][C:12]([F:11])([F:32])[C:13]([C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=3)=[O:8])[CH2:28][CH2:27]2)=[CH:23][CH:24]=1)([OH:18])[C:14]([F:17])([F:16])[F:15]

参加物

6

反応物 4

HCID 1354-Hydroxybenzoic AcidHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

生成物 1

HCID 86638568HCID 86638568、化合物収率 9.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-Hydroxybenzoic acid (2.045 mmol, 0.282 g), 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol (2.045 mmol, 0.7 g) and triethylamine (6.14 mmol, 0.853 mL, 0.621 g) were combined and stirred at room temperature in dichloromethane (5 mL). 1-Propanephosphonic acid cyclic anhydride (3.07 mmol, 1.826 mL, 1.952 g; 50% solution in ethyl acetate) was added and the reaction stirred for 2 hours. The reaction mixture was washed with saturated sodium bicarbonate solution and the organic layer dried over magnesium sulphate and concentrated under vacuum. The residue was dissolved in dichloromethane with a few drops of methanol and purified by column chromatography (dichloromethane—6% methanol in dichloromethane) to afford the title compound (90 mg). MS (ESI) m/z 463.0 [M+H]+

後処理

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialthe organic layer dried over magnesium sulphate
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane with a few drops of methanol
  5. custompurified by column chromatography (dichloromethane—6% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-1e37f71bf7a14fbe9d4f72e059cd3e30
出典データセット
uspto-grants-2013_01
特許番号
US08357679B2

反応ノート

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