Trifluoroacetic acid → HCID 21029346, compound

HRID 1828757Notes

Reaction equation

HRID 1828757 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-217adfd0a51849dfa5a1740e03f08e1c
Source dataset
uspto-grants-2006_06
Patent number
US07060702B2

Reaction notes

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