Boron trifluoride etherate → HCID 86591198, compound

HRID 1827678Notes

Reaction equation

HRID 1827678 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[N:28][CH:29]=1)[CH2:6][CH2:7][C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[N:14]=1)[CH3:2].[CH2:33]([SH:36])[CH2:34][SH:35].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>CC(O)=O>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:24]1[CH:25]=[N:26][C:27]([O:30][CH3:31])=[N:28][CH:29]=1)[CH2:6][CH2:7][C:8]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[CH2:19][CH2:18][CH2:17][NH:16][C:15]=3[N:14]=2)[S:36][CH2:33][CH2:34][S:35]1)[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 69396468HCID 69396468, compound

Product 1

HCID 86591198HCID 86591198, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 3-3a (7.6 g, 17.4 mmol) and 1,2-ethanedithiol (17.5 mL, 208.6 mmol) in 25 mL AcOH was added BF3.OEt2 (17.5 mL, 138.1 mmol) dropwise at 0° C. under nitrogen. The reaction mixture was stirred at 0 C for 0.5 hr, then at rt for 3.5 hr. The reaction mixture was slowly poured into ice-cooled 300 mL NaHCO3 (sat.) and extracted with diethyl ether (2×200 mL). The organic layers were combined and washed with brine and dried over Na2SO4. After removal of the solvent, the residue was purified by flash chromatography on silica gel (100% EtOAc) to afford the desired product 4-1a as an oil.

Workup

  1. waitat rt for 3.5 hr
  2. additionThe reaction mixture was slowly poured into ice-
  3. extractionextracted with diethyl ether (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removal of the solvent
  7. customthe residue was purified by flash chromatography on silica gel (100% EtOAc)

Sources & evidence

ORD record
ord-d2bcf9f8de4640e0bfee46a9b84dd0a9
Source dataset
uspto-grants-2006_06
Patent number
US07056909B2

Reaction notes

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