Ethylene Glycol → HCID 101174828, compound

HRID 1731829Notes

Reaction equation

HRID 1731829 reaction equation
[C:1](=[O:4])(O)[O-:2].[Na+].[CH3:6][C@@H:7]1[C@@H:17]([C@@H:18](/[CH:20]=[C:21](/[CH:23]=[CH:24]/C(/O)=C2/C([C@H]([C@@H](C(NC)=O)C)N([C@H]3O[C@@H](C)[C@@H](O)CC3)C/2=O)=O)\[CH3:22])[CH3:19])O[C@@]2(C)[O:15][C@@H:8]1[CH:9]=[CH:10][C@@:11]12O[CH2:12]1.I([O-])(=O)(=O)=O.[Na+].[CH2:55]([OH:58])[CH2:56]O.[OH2:59]>C(O)(C)(C)C>[CH3:6][C@H:7]1[C@H:17]([C@@H:18](/[CH:20]=[C:21](/[CH:23]=[CH:24]/[C:1]([OH:2])=[O:4])\[CH3:22])[CH3:19])[O:58][C@:55]2([CH3:56])[O:15][C@H:8]1[CH:9]=[CH:10][C@:11]12[O:59][CH2:12]1

Participants

7

Reactant 5

HCID 174Ethylene GlycolHCID 962Water3×HCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 54708748Streptolydigin

Product 1

HCID 101174828HCID 101174828, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
5 °C

Procedure

Sodium bicarbonate (0.54 g, 6.43 mmol) in water (10 mL) was added to a stirred solution of streptolydigin (3.86 g, 6.43 mmol) in t-butyl alcohol (600 mL) and deionized water (400 mL). The solution was cooled to 5° C., a solution of sodium periodate (24 g) in water (1100 mL) was added and the temperature was maintained at 5° C. for 27 h, while the reaction mixture was protected from light. Ethylene glycol (16 mL) was added and the solution was extracted with ether, dried and concentrated. The crude material was purified by partition chromatography over Celite to yield streptolic acid.

Workup

  1. temperaturethe temperature was maintained at 5° C. for 27 h, while the reaction mixture
  2. extractionthe solution was extracted with ether
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified
  6. customby partition chromatography over Celite

Sources & evidence

ORD record
ord-b7a63c89f5d74c12afa3ffe7d9d2af19
Source dataset
uspto-grants-1986_11
Patent number
US04623644

Reaction notes

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