Trifluoroacetic acid → HCID 46916266, compound

HRID 2207757Notes

Reaction equation

HRID 2207757 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-1e49046660a445c699d936e4d7c22743
Source dataset
uspto-grants-2016_06
Patent number
US09376452B2

Reaction notes

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