N-Hydroxysuccinimide → HCID 57824469, compound

HRID 1943581Notes

Reaction equation

HRID 1943581 reaction equation
[CH3:1][O:2][C@H:3]([C@@H:6]([C@H:9]([C@H:12]([CH3:14])[OH:13])[O:10][CH3:11])[O:7][CH3:8])[CH:4]=[O:5].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][O:2][C@@H:3]1[C@H:6]([O:7][CH3:8])[C@@H:9]([O:10][CH3:11])[C@H:12]([CH3:14])[O:13][C@H:4]1[O:5][N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22]

Participants

5

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 14104333HCID 14104333, compound

Product 1

HCID 57824469HCID 57824469, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a stirred solution of 2,3,4-tri-O-methyl-L-rhamnose (6.5 g, 31.5 mmol) and N-hydroxysuccinimide (5.4 g, 47 mmol) in benzene (50 mL) was added p-toluenesulfonic acid (50 mg, cat.). The solution was heated to reflux and water (H2O) was collected using a Dean-Stark trap. After 4 h, the solution was cooled and the supernatant toluene layer was separated from a small amount of insoluble gum. The organic layer was washed with a saturated solution of sodium bicarbonate (NaHCO3; 20 mL), then dried over MgSO4 and concentrated to a solid. Recrystallization from ether (Et2O)-hexanes gave the title compound (4.95 g, 52%) as an off-white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customwater (H2O) was collected
  4. temperaturethe solution was cooled
  5. customthe supernatant toluene layer was separated from a small amount of insoluble gum
  6. washThe organic layer was washed with a saturated solution of sodium bicarbonate (NaHCO3; 20 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to a solid
  9. customRecrystallization from ether (Et2O)-hexanes

Sources & evidence

ORD record
ord-331830e7bdfc4966a8d51cf0d3d45264
Source dataset
uspto-grants-2013_03
Patent number
US08394774B2

Reaction notes

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