Hydrochloric Acid → HCID 59430951, compound

HRID 505683Notes

Reaction equation

HRID 505683 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=C(CO[C@H](C)C(N3CCOCC3)=O)[CH:15]=1)[C:6]([CH3:32])=[C:5]2[C:33]([C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1)=[O:34].[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1.[OH-:47].[Li+].Cl.[CH3:50][OH:51]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:15]=[C:42]([CH:17]=[CH:18][CH:19]=1)[CH2:46][O:45][C@H:44]([CH3:43])[C:50]([OH:51])=[O:47])[C:6]([CH3:32])=[C:5]2[C:33](=[O:34])[C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59430969HCID 59430969, compound

Product 1

HCID 59430951HCID 59430951, compoundYield 92%

Procedure

The compound of Example 39-1 (114 mg, 0.20 mmol) was dissolved in methanol (0.75 ml) and THF (0.75 ml) and thereto was added 2N aqueous lithium hydroxide solution (0.2 ml), followed by stirring under reflux for 4 hours. After being cooled to room temperature, the solution was adjusted around pH2 with 1N diluted hydrochloric acid. The solution was extracted with ethyl acetate and the organic layer was washed with saturated brine, dried over magnesium sulfate and filtered. The solvent was removed in vacuo to give the subject compound (99 mg, 92%).

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d082d286646f43629347b2900fa3ffc2
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

Loading…