Hydrochloric Acid → HCID 51557049, compound

HRID 1744688Notes

Reaction equation

HRID 1744688 reaction equation
C([C@H]1COC(=O)N1C([C@@H:16]1[C@H:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:19][N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17]1)=O)C1C=CC=CC=1.[OH-:35].[Li+].OO.S([O-])([O-])=O.[Na+].[Na+].Cl.[O:46]1[CH2:50]CCC1.O>>[C:31]([O:30][C:28]([N:18]1[CH2:19][C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C@@H:16]([C:50]([OH:46])=[O:35])[CH2:17]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 21881883Oxolane--water (1/1)HCID 86592419HCID 86592419, compound

Product 1

HCID 51557049HCID 51557049, compound

Procedure

To a cooled (0° C.) solution of the product of step C (835 mg; 1.78 mmol) lithium hydroxide (85 mg; 3.56 mmol) in 15 mL of a 4:1 mixture of tetrahydrofuran-water was added a 30% aqueous solution of hydrogen peroxide. After 5 min, the solution was warmed to ambient temperature and stirred for 5 h. The reaction mixture was poured into a 10% aqueous solution of sodium sulfite and then acidified to pH 3 with 1 N hydrochloric acid. The aqueous solution was extracted three times with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), filtered, concentrated in vacuo and the crude acid was purified on silica gel (30% ethyl acetate/hexane with 1% acetic acid) which furnished 520 mg of the title compound.

Workup

  1. extractionThe aqueous solution was extracted three times with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe crude acid was purified on silica gel (30% ethyl acetate/hexane with 1% acetic acid) which

Sources & evidence

ORD record
ord-17dfbb5fdd5b43038541bc24acf8e0f7
Source dataset
uspto-grants-2006_03
Patent number
US07015235B2

Reaction notes

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