Sulfuryl chloride → HCID 21700739, compound

HRID 1597663Notes

Reaction equation

HRID 1597663 reaction equation
S(Cl)(Cl)(=O)=O.Br.C[O:8][C:9](=[O:33])[CH:10]([NH:16][S:17]([C:20]1[CH:32]=[CH:31][C:23]2[O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:22]=2[CH:21]=1)(=[O:19])=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]>ClCCl.C(N(CC)CC)C>[CH:21]1[C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][C:23]=2[CH:31]=[CH:32][C:20]=1[S:17]([NH:16][CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:23](=[O:24])[CH:22]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:25]=1)[CH2:21][CH3:20])[C:9]([OH:8])=[O:33])(=[O:18])=[O:19]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 70062513HCID 70062513, compound

Product 1

HCID 21700739HCID 21700739, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The appropriate sulfonyl chloride (1.5 equivalents, 0.18 mmol) and 70 mg of a morpholino-resin (prepared according to Booth and Hodges, Supra., 1997) were mixed in 1 mL dichloromethane in each of 10 different vials. One milliliter of a 0.12 M stock solution of 6-amino-2-(dibenzofuran-2-sulfonylamino)-hexanoic acid methyl ester hydrobromide in triethylamine was added to each of the vials. The vials were sealed and shaken for 16 hours at room temperature. An excess of an amino-resin and an isocyanato-resin (also both prepared according to Booth and Hodges, Supra, 1997) was added to each vial and shaken for 16 hours to quench unreacted starting materials. Each reaction was filtered through a plug of glass wool, and the resins were washed with 2 mL tetrahydrofuran. The filtrate was evaporated under a stream of nitrogen, and the residue in each vial was redissolved in 1 mL dioxane. One milliliter of a 0.6 M aqueous solution of lithium hydroxide was added, and the resulting mixtures were shaken for 16 hours. Each reaction was washed with diethyl ether, and the aqueous layer was then acidified with 1 molar hydrochloric acid. The reactions were extracted with ethyl acetate and evaporated under a stream of nitrogen to leave the expected products. The compounds were analyzed by LC/MS to determine purity and presence of expected molecular ion.

Workup

  1. customThe vials were sealed
  2. additionwas added to each vial and
  3. stirringshaken for 16 hours
  4. customto quench unreacted
  5. filtrationEach reaction was filtered through a plug of glass wool
  6. washthe resins were washed with 2 mL tetrahydrofuran
  7. customThe filtrate was evaporated under a stream of nitrogen
  8. dissolutionthe residue in each vial was redissolved in 1 mL dioxane
  9. additionOne milliliter of a 0.6 M aqueous solution of lithium hydroxide was added
  10. stirringthe resulting mixtures were shaken for 16 hours
  11. washEach reaction was washed with diethyl ether
  12. extractionThe reactions were extracted with ethyl acetate
  13. customevaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-d3baf6ffc551436d8f3bdbe2e7dadd7a
Source dataset
uspto-grants-2001_09
Patent number
US06294674B1

Reaction notes

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