4-Toluenesulfonyl chloride → HCID 19434076, compound

HRID 1736026Notes

Reaction equation

HRID 1736026 reaction equation
O[CH2:2][C:3]1[N:4]([CH:18]([CH3:20])[CH3:19])[S:5](=[O:17])(=[O:16])[C:6]2[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][C:7]=2[CH:8]=1.C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:39]([NH2:42])[C:40]#[CH:41]>C1COCC1>[CH3:19][CH:18]([N:4]1[C:3]([CH2:2][NH:42][CH2:39][C:40]#[CH:41])=[CH:8][C:7]2[CH:9]=[C:10]([S:12]([NH2:15])(=[O:14])=[O:13])[S:11][C:6]=2[S:5]1(=[O:17])=[O:16])[CH3:20]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 239041PropargylamineHCID 19434080HCID 19434080, compound

Product 1

HCID 19434076HCID 19434076, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 15, Step E (1.40 g, 4.14 mmol) and triethylamine (1.26 g, 12.4 mmol) in anhydrous THF (80 mL) at 0° C. was added p-toluenesulfonyl chloride (1.18 g, 6.21 mmol) and the mixture was maintained at this temperature for 20 h. Propargylamine (3 mL) was added to the reaction mixture which was stirred for an additional 18 h. The reaction mixture was evaporated to a residue which was mixed with 2N HCl (60 mL) and this mixture was extracted with ethyl acetate (2×50 mL). The aqueous layer was separated and adjusted to pH 7.5 by the addition of a saturated aqueous solution of sodium bicarbonate (100 mL) followed by extraction with ethyl acetate (2×60 mL). The combined extracts were dried (MgSO4), filtered, and evaporated to a residue which was purified by column chromatography (silica, 50% to 75% ethyl acetate/hexane) to give an oil which crystallized from methylene chloride/hexane to provided an off-white solid (0.61 g, 39%): mp 133°-135° C. Analysis: Calculated for C13H17N3O4S3 : C, 41.58; H, 4.60; N, 11.11. Found: C, 41.42; H, 4.60;0N, 11.11.

Workup

  1. temperaturethe mixture was maintained at this temperature for 20 h
  2. customThe reaction mixture was evaporated to a residue which
  3. additionwas mixed with 2N HCl (60 mL)
  4. extractionthis mixture was extracted with ethyl acetate (2×50 mL)
  5. customThe aqueous layer was separated
  6. additionadjusted to pH 7.5 by the addition of a saturated aqueous solution of sodium bicarbonate (100 mL)
  7. extractionfollowed by extraction with ethyl acetate (2×60 mL)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated to a residue which
  11. customwas purified by column chromatography (silica, 50% to 75% ethyl acetate/hexane)
  12. customto give an oil which
  13. customcrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-5d7a5a28cbed4318bb5b84929ec0abd6
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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