Ethyl Acetate → HCID 86758771, compound

HRID 1633530Notes

Reaction equation

HRID 1633530 reaction equation
C([O:9][C@@H:10]1[C@@H:15]([CH2:16][C:17]([O:19]C)=[O:18])[C@@H:14]([O:21]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:30][O:31]C(=O)C2C=CC=CC=2)[O:12][C@H:11]1[O:40][CH2:41][C@H:42]([NH:77][C:78](=[O:96])[CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH3:95])[C@H:43]([O:59][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])(=O)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>ClCCl>[C:17]([CH2:16][C@H:15]1[C@@H:14]([OH:21])[C@@H:13]([CH2:30][OH:31])[O:12][C@@H:11]([O:40][CH2:41][C@H:42]([NH:77][C:78](=[O:96])[CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH3:95])[C@H:43]([OH:59])/[CH:44]=[CH:45]/[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C@@H:10]1[OH:9])([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86758772HCID 86758772, compound

Product 1

HCID 86758771HCID 86758771, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The compound (6) (176 mg, 130 μmol) was dissolved in dichloromethane (3 ml), followed by cooling to 0° C. Tetrabutylammonium fluoride (TBAF, 188 μl) was added and the mixture was stirred at room temperature for 24 hours. After confirming the completion of the reaction using TLC (AcOEt/Hex=1/2), the reaction mixture was concentrated under reduced pressure and the residue was dissolved in methanol (5 ml). A catalytic amount of sodium methoxide was added and the mixture was stirred at 40° C. for 24 hours. Further, water was added, followed by stirring for 24 hours. After confirming the completion of the reaction using TLC (CHCl3/MeOH/H2O=5/4/1), the reaction mixture was neutralized with an ion-exchange resin Amberlite IR-120 (H+), followed by removing the resin by filtration. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting syrup was purified by gel filtration (Sephadex LH-20, CHCl3/MeOH/H2O=5/4/0.7) to give a compound (1a) (78 mg, 90%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (5 ml)
  3. additionA catalytic amount of sodium methoxide was added
  4. stirringthe mixture was stirred at 40° C. for 24 hours
  5. additionFurther, water was added
  6. stirringby stirring for 24 hours
  7. customby removing the resin
  8. filtrationby filtration
  9. concentrationconcentrated under reduced pressure
  10. filtrationThe resulting syrup was purified by gel filtration (Sephadex LH-20, CHCl3/MeOH/H2O=5/4/0.7)

Sources & evidence

ORD record
ord-9b5b49127ff74049a33cffeb5c05e41d
Source dataset
uspto-grants-2003_01
Patent number
US06503885B1

Reaction notes

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