Trifluoroacetic acid → HCID 70869080, compound

HRID 1844724Notes

Reaction equation

HRID 1844724 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:18]2[N:19]([CH2:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[C:20]([CH3:27])=[C:21]([S:23](=[O:26])(=[O:25])[NH2:24])[CH:22]=2)[CH:17]=1)[C:8]([O:10]C(C)(C)C)=[O:9])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:18]2[N:19]([CH2:28][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[C:20]([CH3:27])=[C:21]([S:23](=[O:26])(=[O:25])[NH2:24])[CH:22]=2)[CH:17]=1)[C:8]([OH:10])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86719137HCID 86719137, compound

Product 1

HCID 70869080HCID 70869080, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 13a (180 mg, 0.37 mmol) was treated with a mixture of TFA (0.5 mL) and DCM (5 mL) and stirred at rt overnight. After the reaction was complete (monitored by LC-MS), the mixture was concentrated to give compound 13b (145 mg, 91%). 1H-NMR (400 MHz, CDCl3) δ: 8.12 (s, 1H), 7.88 (s, 1H), 7.58 (s, 1H), 6.51 (s, 1H), 4.77-4.75 (m, 2H), 3.76 (m, 2H), 2.56 (s, 3H), 1.53 (s, 3H), 1.37-1.35 (m, 12H), 1.00-0.99 (m, 3H), 0.64-0.63 (m, 2H). MS Found: 433 (M+1).

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-26511f60c7c442748c846618b2889d3a
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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