2,6-Lutidine → HCID 10237940, compound

HRID 2211694Notes

Reaction equation

HRID 2211694 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[O:13]=[S:14]1(=[O:41])[CH:19]=[CH:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:30][C@H:29]([CH2:31][NH:32]C(=O)OC(C)(C)C)[O:28][C:27]3=[O:40])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1.N1C(C)=CC=CC=1C.C(N(C(C)C)CC)(C)C.C1(C(C2C=CC=CC=2)CCO[C:69](=[S:73])[CH:70]([F:72])[F:71])C=CC=CC=1>ClCCl.CO>[O:41]=[S:14]1(=[O:13])[CH:19]=[CH:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:30][C@H:29]([CH2:31][NH:32][C:69](=[S:73])[CH:70]([F:72])[F:71])[O:28][C:27]3=[O:40])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1

Participants

8

Reactant 5

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 81531DiisopropylethylamineHCID 21874093HCID 21874093, compoundHCID 59997913HCID 59997913, compound

Product 1

HCID 10237940HCID 10237940, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Trimethylsilyl trifluoromethanesulfonate (0.26 mL, 1.41 mmol) is added slowly over 15 min to a solution of the product from Step 7 (0.30 g, 0.71 mmol) and 2,6-lutidine (0.25 mL, 2.1 mmol) in dichloromethane (1.5 mL). The solution is stirred at room temperature for 1 h and then treated with methanol (1 mL). After 30 min, the solution is concentrated and redissolved in methanol (4 mL) and diisopropylethyl amine (0.38 mL, 2.1 mmol) is added. A solution of difluoro-thioacetic acid O-(3,3-diphenyl-propyl) ester (0.325 g, 0.71 mmol) in dichloromethane (0.5 mL) is then added and the solution stirred for 20 h at room temperature. The reaction mixture is then concentrated and the residue purified by column chromatography (0–1% MeOH-DCM) to provide the title compound.

Workup

  1. waitAfter 30 min
  2. concentrationthe solution is concentrated
  3. dissolutionredissolved in methanol (4 mL)
  4. stirringthe solution stirred for 20 h at room temperature
  5. concentrationThe reaction mixture is then concentrated
  6. customthe residue purified by column chromatography (0–1% MeOH-DCM)

Sources & evidence

ORD record
ord-2f87fc6b8e0a41dfa1ef08a99eec0bc9
Source dataset
uspto-grants-2006_09
Patent number
US07101874B2

Reaction notes

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