Trifluoroacetic acid → HCID 118223417, compound

HRID 2200204Notes

Reaction equation

HRID 2200204 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]4[CH:25]=[C:26]([CH:34]([N:36]5[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]5)[CH3:35])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=4)=[O:22])=[CH:16][C:15]=3[F:49])[CH:10]=[CH:9][N:8]=2)=[O:5])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:49][C:15]1[CH:16]=[C:17]([NH:20][C:21](=[O:22])[NH:23][C:24]2[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=[C:26]([CH:34]([N:36]3[CH2:37][CH2:38][NH:39][CH2:40][CH2:41]3)[CH3:35])[CH:25]=2)[CH:18]=[CH:19][C:14]=1[O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([NH:6][C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118223399HCID 118223399, compound

Product 1

HCID 118223417HCID 118223417, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the compound obtained in Step 1 (230 mg, 0.33 mmol) in DCM (15 mL), add trifluoroacetic acid (400 mg), stir at room temperature for 2 hrs. Remove the volatiles, partition the residue in EtOAc and saturated NaHCO3 solution, and separate the organic layer, dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=3:1) affords the title compound (173 mg, 88.3%). MS: (M+1): 588.

Workup

  1. customRemove the volatiles
  2. custompartition the residue in EtOAc
  3. customsaturated NaHCO3 solution, and separate the organic layer
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentrate under reduced pressure
  6. customto give the crude product
  7. customPurification by chromatography (silica gel, EtOAc:PE=3:1)

Sources & evidence

ORD record
ord-7f6769ac5d184a429609dd82f88790d9
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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