Trifluoroacetic acid → HCID 57917636, compound

HRID 1878386Notes

Reaction equation

HRID 1878386 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

HCID 57917636HCID 57917636, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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]+

Workup

  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

Sources & evidence

ORD record
ord-f21a159f7bb044fd8f9b3e39699a0b70
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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