Trifluoroacetic acid → HCID 57917636, 화합물

HRID 1878386노트

반응식

HRID 1878386 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 57917636HCID 57917636, 화합물수율 86%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-f21a159f7bb044fd8f9b3e39699a0b70
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314091B2

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