Trifluoroacetic acid → HCID 25221237, compound

HRID 1907757Notes

Reaction equation

HRID 1907757 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([C:21]2[CH:49]=[CH:48][C:24]([C:25]([NH:27][C:28]3[CH:29]=[C:30]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:31]=[CH:32][C:33]=3[NH:34]C(=O)OC(C)(C)C)=[O:26])=[CH:23][CH:22]=2)[CH2:17]1)=O)(C)(C)C>C(Cl)Cl>[NH2:34][C:33]1[CH:32]=[CH:31][C:30]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:29][C:28]=1[NH:27][C:25](=[O:26])[C:24]1[CH:48]=[CH:49][C:21]([N:18]2[CH2:19][CH2:20][C@H:16]([NH2:15])[CH2:17]2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59737479HCID 59737479, compound

Product 1

HCID 25221237HCID 25221237, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of 326 (370 mg, 0.65 mmol) in DCM (1 mL). The reaction mixture was stirred at room temperature for 24 h, concentrated and the residue was partitioned between EtOAc and NaHCO3. The aqueous layer was extracted with fresh EtOAc and the comb organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified using the Biotage system, (cartridge Biotage Si 25+M), eluent MeOH/DCM (10% to 40%) to afford the title compound 327 (161 mg, 67% yield).

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between EtOAc and NaHCO3
  3. extractionThe aqueous layer was extracted with fresh EtOAc
  4. washthe comb organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-c651111721134af1a8778c352f0a0c97
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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