Propylene Oxide → HCID 88835350, compound

HRID 1287592Notes

Reaction equation

HRID 1287592 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14]([OH:17])[CH2:15][S:16][C@H:11]12)=[O:8].CC(N(C)C)=O.C1OC1C.[CH2:43]([S:45](Cl)(=[O:47])=[O:46])[CH3:44]>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=3)=[O:19])=[C:14]([O:17][S:45]([CH2:43][CH3:44])(=[O:47])=[O:46])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 11667Ethanesulfonyl chlorideHCID 31374DimethylacetamideHCID 70559815p-Nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 88835350HCID 88835350, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

By following the procedure described by Example 4, 4.7 g. (10 mmole) of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate was reacted for about 3 hours in 50 ml. of dimethylacetamide containing about 2 ml. of propylene oxide with a stoichiometric amount of ethanesulfonyl chloride. The reaction mixture was dissolved in ethyl acetate and the solution washed with a saturated solution of sodium chloride. The organic phase was dried and evaporated to dryness to provide the reaction product. The product was purified by preparative thin layer chromatography on silica gel by employing 65 percent ethyl acetate/hexane for development. The purified product, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-ethylsulfonyloxy-3-cephem-4-carboxylate, gave the following percent elemental composition on microanalysis for the formula C22H21N3O9S3 :

Workup

  1. washthe solution washed with a saturated solution of sodium chloride
  2. customThe organic phase was dried
  3. customevaporated to dryness
  4. customto provide the reaction product
  5. customThe product was purified by preparative thin layer chromatography on silica gel

Sources & evidence

ORD record
ord-79b7f97be49d4de8ba8912c6519eaf62
Source dataset
uspto-grants-1976_10
Patent number
US03985737

Reaction notes

Loading…