Trifluoroacetic acid → HCID 46916266, compound

HRID 1616695Notes

Reaction equation

HRID 1616695 reaction equation
[C:1]([NH:9][C:10](=[S:28])[NH:11][C:12]1[S:20][C:15]2[CH2:16][O:17][CH2:18][CH2:19][C:14]=2[C:13]=1[C:21]([O:23]C(C)(C)C)=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([NH:9][C:10](=[S:28])[NH:11][C:12]1[S:20][C:15]2[CH2:16][O:17][CH2:18][CH2:19][C:14]=2[C:13]=1[C:21]([OH:23])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 46916262HCID 46916262, compound

Product 1

HCID 46916266HCID 46916266, compoundYield 3.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-Butyl 2-(3-benzoylthioureido)-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.104 g, 0.25 mmol, 1 equiv.) in DCM (10 mL) was added TFA (2 mL, 26 mmol, 100 equiv.), and the reaction was stirred at rt for 16 h. The solvent was removed and the product was triturated with 1:1 Et2O/hexanes (25 mL) and filtered. The product was purified by mass-directed reverse-phase chromatography and isolated as a white solid (3 mg, 3% yield). 1H NMR (400 MHz, CDCl3) δ 14.92 (br s, 1H), 9.02-9.09 (m, 1H), 7.83-7.91 (m, 1H), 7.55-7.66 (m, 2H), 7.41-7.50 (m, 2H), 7.19-7.23 (m, 1H), 4.69-4.76 (m, 2H), 3.92-3.98 (m, 2H), 2.88-3.03 (m, 2H). LCMS retention time: 2.955 min; LCMS purity at 215 nm=100%. HRMS m/z calculated for C16H15N2O4S2 [M++1]: 363.0468. found 363.0464.

Workup

  1. customThe solvent was removed
  2. customthe product was triturated with 1:1 Et2O/hexanes (25 mL)
  3. filtrationfiltered
  4. customThe product was purified by mass-directed reverse-phase chromatography

Sources & evidence

ORD record
ord-ffb646b69b884c278b3152b4868a4ea2
Source dataset
uspto-grants-2014_07
Patent number
US08765803B1

Reaction notes

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