Trifluoroacetic acid → HCID 22036441, compound

HRID 1789746Notes

Reaction equation

HRID 1789746 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[C:15]([O:22][CH2:23][CH2:24][O:25][C:26]3[C:27]([N:32]4[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]4)=[N:28][CH:29]=[CH:30][N:31]=3)[CH:16]=[CH:17][CH:18]=2)[N:13]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[N:32]1([C:27]2[C:26]([O:25][CH2:24][CH2:23][O:22][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[N:13]=[C:12]([NH:11][C:8](=[O:10])[CH3:9])[CH:21]=[CH:20]4)=[N:31][CH:30]=[CH:29][N:28]=2)[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22036474HCID 22036474, compound

Product 1

HCID 22036441HCID 22036441, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TFA (1.5 mL) was added to a solution of the product from Step 2 (112 mg, 0.22 mmol) in CH2Cl2(1.5 mL) at 0° C. and the mixture was stirred under inert atmosphere for 1 h. The reaction mixture was diluted with CH2Cl2 and washed with 2 M aqueous NaOH (×4) and brine. The organic layer was dried (MgSO4) and concentrated. The crude solid product (83 mg) was purified by column chromatography on silica using CHCl3/MeOH (9:1)+1% NH3 as eluent to give the title compound as an oil that solidified after repeated additions of pentane: yield 67 mg (75%); MS m/z 409 (M+H)+. Anal. (C21H24N6O3.0.6H2O.0.1C5H12) C, H, N.

Workup

  1. washwashed with 2 M aqueous NaOH (×4) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude solid product (83 mg) was purified by column chromatography on silica

Sources & evidence

ORD record
ord-21bc5e2924824050abb3a8a5e423700e
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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