Boron trifluoride etherate → HCID 86615014, compound

HRID 1436683Notes

Reaction equation

HRID 1436683 reaction equation
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12](=[O:34])[C:13]1[CH:25]=[C:24]([C:26](=O)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[C:15]([C:16]([N:18]([CH3:22])[CH2:19][CH2:20][CH3:21])=[O:17])[CH:14]=1.[CH2:35]([SH:39])[CH2:36][CH2:37][SH:38]>ClCCl>[CH3:10][O:11][C:12](=[O:34])[C:13]1[CH:25]=[C:24]([C:26]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[S:39][CH2:35][CH2:36][CH2:37][S:38]2)[CH:23]=[C:15]([C:16]([N:18]([CH3:22])[CH2:19][CH2:20][CH3:21])=[O:17])[CH:14]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 68814475HCID 68814475, compound

Product 1

HCID 86615014HCID 86615014, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron trifluoride diethyl etherate (0.358 mL, 2.83 mmol) to a solution of 5-benzoyl-N-methyl-N-propyl-isophthalamic acid methyl ester (0.192 g, 0.566 mmol) in dichloromethane (3 mL) at 0° C. Add 1,3-propanedithiol (0.114 mL, 1.12 mmol). Stir at room temperature overnight. Partition between water (20 mL) and dichloromethane (20 mL) and extract the aqueous layer with dichloromethane (20 mL). Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes) to give the title compound (51%).

Workup

  1. customPartition between water (20 mL) and dichloromethane (20 mL)
  2. extractionextract the aqueous layer with dichloromethane (20 mL)
  3. dry with materialDry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-7a375fd892a14dfb8400bd4f1f7486c5
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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