Trifluoroacetic acid → HCID 46916263, compound

HRID 1616699Notes

Reaction equation

HRID 1616699 reaction equation
[C:1]([NH:9][C:10](=[S:29])[NH:11][C:12]1[S:21][C:15]2[CH2:16][O:17][CH:18]([CH3:20])[CH2:19][C:14]=2[C:13]=1[C:22]([O:24]C(C)(C)C)=[O:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:9][C:10](=[S:29])[NH:11][C:12]1[S:21][C:15]2[CH2:16][O:17][CH:18]([CH3:20])[CH2:19][C:14]=2[C:13]=1[C:22]([OH:24])=[O:23])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731951HCID 86731951, compound

Product 1

HCID 46916263HCID 46916263, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 2-(3-benzoylthioureido)-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.028 g, 0.065 mmol, 1 eq.) was added a 40% v/v solution of trifluoroacetic acid in dichloromethane (2.5 mL). After stirring the solution for 4 hours at rt, the solvent was evaporated in vacuo, and the residue purified by reverse-phase chromatography to yield the product as a white semi-solid (0.011 g, 0.029 mmol, 46% yield). 1H NMR (400 MHz, Acetone) δ 8.07 (d, J=7.4, 2H), 7.68 (t, J=7.0, 1H), 7.56 (t, J=7.5, 2H), 4.76 (q, J=14.7, 2H), 3.82-3.68 (m, 1H), 3.05 (d, 1H), 1.47 (d, J=6.5, 1H), 1.32 (d, J=6.1, 3H). 13C NMR (126 MHz, Acetone) δ 175.37, 166.92, 165.37, 161.89, 148.65, 134.12, 133.28, 131.39, 129.62, 129.28, 126.49, 71.61, 65.11, 35.05, 21.82. LCMS retention time: 3.095 min; Purity at 214 nm=93.3%. HRMS m/z calculated for C17H17N2O4S2 [M++1] 377.0624. found 377.0622.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe residue purified by reverse-phase chromatography

Sources & evidence

ORD record
ord-125ee3bb554349b198f4ab34dae31564
Source dataset
uspto-grants-2014_07
Patent number
US08765803B1

Reaction notes

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