Thionyl Chloride → HCID 22626243, compound

HRID 277979Notes

Reaction equation

HRID 277979 reaction equation
FC(F)(F)S(O[C:7]1[CH:17]=[CH:16][C:15]([C:18](=[O:24])[NH:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:14][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=O)=O.S(Cl)(Cl)=O>C(OCC)(=O)C>[CH3:22][CH:21]([CH3:23])[CH2:20][NH:19][C:18]([C:15]1[CH:16]=[CH:17][C:7]([C:7]2[C:8]([C:9]([OH:11])=[O:10])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:14]=1)=[O:24]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22626301HCID 22626301, compound

Product 1

HCID 22626243HCID 22626243, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

4′-((2-methylpropyl)carbamoyl)-2′-ethoxycarbonyl-2-biphenyl carboxylic acid (1.0 g) which was prepared by the same procedure as a series of reaction of Reference Example 4→Reference Example 5, using ethyl 2-trifluoromethylsulfonyloxy-5-((2-methylpropyl)carbamoyl)benzoate, was dissolved into ethyl acetate (20 ml). Thionyl chloride (0.22 ml) was dropped into the above solution. The mixture was stirred for 15 minutes at 50° C. The reaction mixture was cooled to room temperature, and concentrated. A solution of the prepared acyl chloride compound in methylene chloride (10 ml) and triethylamine (0.57 ml) were added to a solution of 4-(N2-t-butoxycarbonyloxyamidino)aniline in methylene chloride (10 ml) at 0° C. The mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (150 ml), and washed with a saturated aqueous solution of sodium chloride (75 ml, 2 times). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (methylene chloride:methanol=100:1) to give the present compound (1.56 g) having the following physical data.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additionA solution of the prepared acyl chloride compound in methylene chloride (10 ml) and triethylamine (0.57 ml) were added to a solution of 4-(N2-t-butoxycarbonyloxyamidino)aniline in methylene chloride (10 ml) at 0° C
  4. stirringThe mixture was stirred for 1 hour at room temperature
  5. additionThe reaction mixture was diluted with ethyl acetate (150 ml)
  6. washwashed with a saturated aqueous solution of sodium chloride (75 ml, 2 times)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (methylene chloride:methanol=100:1)

Sources & evidence

ORD record
ord-af250ad38c4e43569d005e76945a5108
Source dataset
uspto-grants-2002_03
Patent number
US06358960B1

Reaction notes

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