4-Toluenesulfonyl chloride → HCID 178480573, compound

HRID 1736040Notes

Reaction equation

HRID 1736040 reaction equation
O[CH2:2][C:3]1[N:4]([CH3:18])[S:5](=[O:17])(=[O:16])[C:6]2[CH:11]=[C:10](S(N)(=O)=O)[S:9][C:7]=2[CH:8]=1.C([N:21](CC)CC)C.[S:26](Cl)(C1C=CC(C)=CC=1)(=[O:28])=[O:27].[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C1COCC1>[CH3:18][N:4]1[C:3]([CH2:2][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[CH:8][C:7]2[SH:9]([S:26]([NH2:21])(=[O:27])=[O:28])[CH:10]=[CH:11][C:6]=2[S:5]1(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8083MorpholineHCID 8471TriethylamineHCID 19434019HCID 19434019, compound

Product 1

HCID 178480573HCID 178480573, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step F (0.78 g, 2.52 mmol) and triethylamine (1.02 g, 10.1 mmol) in anhydrous THF (30 mL) at ambient temperature was added tosyl chloride (0.961 g, 5.04 mmol). After stirring for 4.5 h, morpholine (2 mL) was added and the mixture was stirred for 1 h followed by heating at reflux temperature for 10 min. The volatiles were evaporated and a saturated solution of sodium bicarbonate (80 mL) was added. This mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried (MgSO4) and evaporated to a viscous oil which was purified by column chromatography (silica, 5% to 10% methanol/methylene chloride) to give a solid (0.41 g 43%). Recrystallization from ethyl acetate/methylene chloride gave a yellowish solid: mp 192°-194° C. Analysis. Calculated for C12H17N3O5S3 : C, 37.98; H, 4.52; N, 11.07. Found: C, 38.09; H, 4.53; N, 11.09.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. temperatureby heating
  3. temperatureat reflux temperature for 10 min
  4. customThe volatiles were evaporated
  5. additiona saturated solution of sodium bicarbonate (80 mL) was added
  6. extractionThis mixture was extracted with ethyl acetate (2×100 mL)
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. customevaporated to a viscous oil which
  9. customwas purified by column chromatography (silica, 5% to 10% methanol/methylene chloride)
  10. customto give a solid (0.41 g 43%)
  11. customRecrystallization from ethyl acetate/methylene chloride
  12. customgave a yellowish solid

Sources & evidence

ORD record
ord-c480530d040d4841898a87da05fb3489
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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