Trifluoroacetic acid → HCID 57917636、化合物

HRID 1878386ノート

反応式

HRID 1878386 の反応式
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[CH:19]([C@H:22]1[CH2:27][NH:26][CH2:25][CH2:24][N:23]1C(OC(C)(C)C)=O)([CH3:21])[CH3:20].[NH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][C:37]=1[F:45].C(N(CC)CC)C.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[NH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([N:26]2[CH2:25][CH2:24][NH:23][C@@H:22]([CH:19]([CH3:20])[CH3:21])[CH2:27]2)=[O:41])=[CH:38][C:37]=1[F:45]

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 17750439(2S)-2-Isopropylpiperazine, N1-BOC protected

生成物 1

HCID 57917636HCID 57917636、化合物収率 86%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-Propanephosphonic acid cyclic anhydride (1.752 mmol. 1.043 ml, 1115 mg) was added to a solution of (S)-tert-butyl 2-isopropylpiperazine-1-carboxylate (0.876 mmol, 200 mg), 4-amino-3-fluorobenzoic acid (0.876 mmol, 136 mg) and triethylamine (1.752 mmol, 0.244 ml, 177 mg) in dichloromethane and stirred at room temperature for 2 hours. After this time, ethyl acetate (100 mL) was then added to the reaction. The organic mixture was washed with saturated sodium hydrogen carbonate, water, dried over sodium sulphate and concentrated under vacuum. The residue was then dissolved in dichloromethane (5 ml) and trifluoroacetic acid (17.52 mmol, 1997 mg) added. The resultant solution was allowed to stand at room temperature overnight. The reaction was concentrated under vacuum and purified by strong cation exchange chromatography to give the title compound (200 mg) as a clear oil. MS (ESI) m/z 266.3 [M+H]+

後処理

  1. washThe organic mixture was washed with saturated sodium hydrogen carbonate, water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was then dissolved in dichloromethane (5 ml)
  5. waitto stand at room temperature overnight
  6. concentrationThe reaction was concentrated under vacuum
  7. custompurified by strong cation exchange chromatography

出典と根拠

ORDレコード
ord-f21a159f7bb044fd8f9b3e39699a0b70
出典データセット
uspto-grants-2012_11
特許番号
US08314091B2

反応ノート

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