Ethanol → HCID 19608501, compound

HRID 1602937Notes

Reaction equation

HRID 1602937 reaction equation
[CH2:1]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[S:16][CH3:17])[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:26]([C:31]([O:33]C)=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)[CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].C(O)C.P([O-])([O-])(O)=O.[Na+].[Na+]>O>[CH2:1]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[S:16][CH3:17])[N:7]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[C:26]([C:31]([OH:33])=[O:32])=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24203Sodium Phosphate, DibasicHCID 19608517HCID 19608517, compound

Product 1

HCID 19608501HCID 19608501, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 270 mg of the product of Example 7, 5 ml of a 5N sodium hydroxide solution and 5 ml of ethanol was stirred for 2 hours at reflux and the mixture was poured into water and acidified with sodium hydrogen phosphate. Extraction was carried out with ethyl acetate and the extracts were washed with water, dried and evaporated to dryness. The residue was chromatographed on silica (eluant: methylene chloride-methanol (9-1)) and the product was impasted in a mixture of 5 ml of ethyl acetate and 5 ml of isopropyl ether to obtain 90 mg of the desired compound melting at 155° C.

Workup

  1. temperatureat reflux
  2. extractionExtraction
  3. washthe extracts were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica (eluant: methylene chloride-methanol (9-1))
  7. additionthe product was impasted in a mixture of 5 ml of ethyl acetate and 5 ml of isopropyl ether

Sources & evidence

ORD record
ord-042a84131dad4300b1353ece12dcddb1
Source dataset
uspto-grants-1999_11
Patent number
US05985894

Reaction notes

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