Trifluoroacetic acid → HCID 24753502, compound

HRID 599835Notes

Reaction equation

HRID 599835 reaction equation
FC(F)(F)C(O)=O.C(OC(O[NH:16][S:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:45]=[CH:46][CH:47]=1)[CH2:24][C:25]1[C:26](=[O:44])[O:27][C:28]2[CH:36]=[C:35]([O:37][C:38](=[O:42])[N:39]([CH3:41])[CH3:40])[C:34]([Cl:43])=[CH:33][C:29]=2[C:30]=1[CH2:31][F:32])(=[O:19])=[O:18])=O)(C)(C)C.C(=O)([O-])O.[Na+]>>[NH2:16][S:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:45]=[CH:46][CH:47]=1)[CH2:24][C:25]1[C:26](=[O:44])[O:27][C:28]2[CH:36]=[C:35]([O:37][C:38](=[O:42])[N:39]([CH3:40])[CH3:41])[C:34]([Cl:43])=[CH:33][C:29]=2[C:30]=1[CH2:31][F:32])(=[O:18])=[O:19]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86637666HCID 86637666, compound

Product 1

HCID 24753502HCID 24753502, compoundYield 100.7%

Procedure

Trifluoroacetic acid (0.1 mL) was added to a solution of dimethylcarbamic acid 3-{3-((tert-butoxycarbonyloxy)aminosulfonyl)aminobenzyl}-6-chloro-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester (compound 1j-1-3-1F-other) (23 mg, 0.039 mmol) in anhydrous dichlromethane (1.0 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was then poured into saturated sodium hydrogen carbonate and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude solid was then obtained by vacuum concentration, and purified by preparative TLC (ethyl acetate:hexane=1:1) to yield the title compound (19 mg, 100%) as a pale yellow powder.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. customA crude solid was then obtained by vacuum concentration
  6. custompurified by preparative TLC (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-873879be382d4133aedb22af95711f39
Source dataset
uspto-grants-2011_03
Patent number
US07897792B2

Reaction notes

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