Toluene → HCID 523407, compound

HRID 1047406Notes

Reaction equation

HRID 1047406 reaction equation
[C:1]1(=[O:12])[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].CN1CCOCC1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22].C1(C)C=CC=CC=1>O1CCCC1.O>[CH3:20][Si:21]([CH3:23])([CH3:22])[O:3][CH:2]1[CH:4]([O:5][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:6]([O:7][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:8]([CH2:9][O:10][Si:21]([CH3:23])([CH3:22])[CH3:20])[O:11][C:1]1=[O:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 7027delta-GluconolactoneHCID 79724-Methylmorpholine

Product 1

HCID 523407HCID 523407, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
17 °C

Procedure

To a solution of D-(+)-glucono-1,5-lactone (21.6 kg) and N-methylmorpholine (98.2 kg) in tetrahydrofuran (192 kg) was added trimethylsilyl chloride (79.1 kg) at 40° C. or below, and then the mixture was stirred at a temperature from 30° C. to 40° C. for 4 hours. After the mixture was cooled to 17° C., toluene (93.6 kg) and water (109 kg) were added thereto. The organic layer was separated and washed with an aqueous solution of 5% sodium dihydrogen phosphate (108 kg×2) and water (108 kg×1). The solvent was evaporated under reduced pressure. To the resulting residue was added tetrahydrofuran (154 kg) and the solvent was evaporated under reduced pressure. Again tetrahydrofuran (154 kg) was added thereto and evaporated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (253 kg) to give a solution of the titled compound in tetrahydrofuran. The purity of the product was 99.0% (conversion rate: 99.1%), which was calculated based on the area ratio measured by HPLC.

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous solution of 5% sodium dihydrogen phosphate (108 kg×2) and water (108 kg×1)
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the resulting residue was added tetrahydrofuran (154 kg)
  5. customthe solvent was evaporated under reduced pressure
  6. additionAgain tetrahydrofuran (154 kg) was added
  7. customevaporated under reduced pressure
  8. dissolutionThe resulting residue was dissolved in tetrahydrofuran (253 kg)

Sources & evidence

ORD record
ord-c9ced2f64c7844ecac3bda04d94b2763
Source dataset
uspto-grants-2013_10
Patent number
US08569520B2

Reaction notes

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