Trifluoroacetic acid → HCID 21029346, compound

HRID 1592959Notes

Reaction equation

HRID 1592959 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:53])([F:52])[C:10]1[CH:11]=[C:12]([CH:45]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:47]=1)[CH2:13][N:14]([CH3:44])[C:15]([N:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]2)[CH2:19][C@@H:18]1[C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[CH3:43])=[O:16]>C(Cl)Cl>[F:53][C:9]([F:8])([F:52])[C:10]1[CH:11]=[C:12]([CH:45]=[C:46]([C:48]([F:49])([F:51])[F:50])[CH:47]=1)[CH2:13][N:14]([CH3:44])[C:15]([N:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]2)[CH2:19][C@@H:18]1[C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=1[CH3:43])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590820HCID 86590820, compound

Product 1

HCID 21029346HCID 21029346, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of intermediate 15b (155 mg) in anhydrous DCM (5 mL). The solution was stirred at r.t. for 3 hours, then it was concentrated in vacuo. The residue was diluted in a saturated potassium carbonate solution (10 mL) and extracted with DCM (2×20 mL) and AcOEt (20 mL). The combined organic extracts were dried and concentrated in vacuo to give the title compound (104 mg) as an oil.

Workup

  1. concentrationit was concentrated in vacuo
  2. additionThe residue was diluted in a saturated potassium carbonate solution (10 mL)
  3. extractionextracted with DCM (2×20 mL) and AcOEt (20 mL)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ba4602014a04b1fb5488fff7ddb15bf
Source dataset
uspto-grants-2007_11
Patent number
US07294630B2

Reaction notes

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