Ethyl Acetate → HCID 131716754, compound

HRID 359890Notes

Reaction equation

HRID 359890 reaction equation
[I-].CN1C=CC=[CH2+]C1[C:9]([C@@:11]1([OH:36])[C@@H:15]([CH:16]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[OH:17])[O:14][C@@H:13]([N:24]2[CH:35]=[C:30]([C:31]([F:34])([F:33])[F:32])[C:28](=[O:29])[NH:27][C:25]2=[O:26])[CH2:12]1)=[O:10].C([O-])(O)=O.[Na+].[O-]S(S([O-])=O)=O.[Na+].[Na+].C(O[CH2:54][CH3:55])(=O)C>O>[CH3:25][N:24]1[CH:55]=[CH:54][CH2:11][C:12]([C:9]([C@@:11]2([OH:36])[C@@H:15]([CH:16]([C:18](=[O:23])[C:19]([CH3:20])([CH3:22])[CH3:21])[OH:17])[O:14][C@@H:13]([N:24]3[CH:35]=[C:30]([C:31]([F:32])([F:34])[F:33])[C:28](=[O:29])[NH:27][C:25]3=[O:26])[CH2:12]2)=[O:10])=[CH:13]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 516892Sodium Bicarbonate

Product 1

HCID 131716754HCID 131716754, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring solution of 100 mg of the product of Example 106 in a mixture of 20 mL of water and 20 mL of ethyl acetate were added 64 mg of NaHCO3 and 115 mg of Na2S2O4 under N2 gas. The resultant mixture was stirred at room temperature for 1 hour, then the organic layer was separated and washed with water. The extract was dried over anhydrous Na2SO4 and evaporated in vacuo. The residue was triturated with a mixture of ether and n-hexane and the yellow needles which formed were collected by suction filtration (50 mg, 62%). The product melted at 168°-170° C. NMR analysis confirmed that the product had the structural formula: ##STR137##

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialThe extract was dried over anhydrous Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was triturated with a mixture of ether and n-hexane
  6. customthe yellow needles which formed
  7. filtrationwere collected by suction filtration (50 mg, 62%)

Sources & evidence

ORD record
ord-78b6db904db04750b0f2ccef35b99ce0
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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