Trifluoroacetic acid → HCID 24753502, compound

HRID 2061118Notes

Reaction equation

HRID 2061118 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+]>ClCCl>[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

5

Reactant 3

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

Product 1

HCID 24753502HCID 24753502, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 dichloromethane (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-77d17a7cc58e4aeb9cead14fb7d6b017
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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