Water → HCID 57752488, compound

HRID 225421Notes

Reaction equation

HRID 225421 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:17])[CH2:11][CH2:12][S:13]([NH2:16])(=[O:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19].O>N1C=CC=CC=1>[CH3:25][C:24]1[CH:26]=[CH:27][C:21]([S:18]([O:17][CH:10]([CH2:11][CH2:12][S:13](=[O:15])(=[O:14])[NH2:16])[CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 20355553HCID 20355553, compound

Product 1

HCID 57752488HCID 57752488, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of hydroxyl-sulfonamide 5 (77 g, 0.30 mol) in pyridine (730 mL, 9.5 vol) was cooled to <10° C. in a 2 L round bottom flask. Tosyl chloride (56.6 g, 0.30 mol) is added to the solution over 5 minutes maintaining the internal temperature below 10° C. The reaction was allowed to warm to room temperature with stirring overnight. The completed reaction was poured into water (10 vol, 770 mL) to give an orange solution which was extracted with iPrOAc/MTBE (1:1, 2×1.5L). The combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL) then brine (1×500 mL). The organic portion was dried (Na2SO4), filtered and evaporated to give sulfonate 6 as an orange oil (78 g).

Workup

  1. temperaturemaintaining the internal temperature below 10° C
  2. customThe completed reaction
  3. customto give an orange solution which
  4. extractionwas extracted with iPrOAc/MTBE (1:1, 2×1.5L)
  5. washThe combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL)
  6. dry with materialThe organic portion was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ee73289096ae43ec94e9d671f56063b1
Source dataset
uspto-grants-2009_07
Patent number
US07557095B2

Reaction notes

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