Triethylamine → HCID 66757518, compound

HRID 1817012Notes

Reaction equation

HRID 1817012 reaction equation
[NH2:1][C@H:2]1[C@@H:7]([CH2:8]O)[CH2:6][CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]1.C(N(CC)CC)C.[N+:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34])([O-:26])=[O:25]>C(Cl)Cl>[N+:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([N:1]1[C@H:2]2[C@H:7]([CH2:6][CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]2)[CH2:8]1)(=[O:35])=[O:34])([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66757455HCID 66757455, compound

Product 1

HCID 66757518HCID 66757518, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Example 61D (39.8 mmol) in CH2Cl2(200 mL) at 0° C. was treated with triethylamine (116.7 mL, 0.120 mol) followed by 2-nitrobenzenesulfonyl chloride (19.5 g, 88.0 mmol). The ice-bath was removed and the solution stirred at ambient temperature for 20 hours. The mixture was concentrated under reduced pressure and the residue dissolved in a mixture of ethanol and 5% aqueous NaOH (2:1, 200 mL). The mixture was stirred for 30 minutes, concentrated under reduced pressure, diluted with ethyl acetate (200 mL) and the layers were separated. The organic layer was dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified via chromatography (SiO2), 50% ethyl acetate/hexanes) to provide the title compound (111.0 g, 27.7 mmol, 70% yield for two steps). MS (DCI/NH3) m/z 415 (M+NH4)+.

Workup

  1. customThe ice-bath was removed
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue dissolved in a mixture of ethanol and 5% aqueous NaOH (2:1, 200 mL)
  4. stirringThe mixture was stirred for 30 minutes
  5. concentrationconcentrated under reduced pressure
  6. additiondiluted with ethyl acetate (200 mL)
  7. customthe layers were separated
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure
  11. customThe residue was purified via chromatography (SiO2), 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-780e1d7f528149ffab7d8ef3c37250c3
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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