Hydrochloric Acid → HCID 20429034, compound

HRID 1759220Notes

Reaction equation

HRID 1759220 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][CH:13]1[C:20](=[O:21])[N:19]2[CH:14]1[S:15][CH2:16][N:17]([S:32]([C:35]([F:38])([F:37])[F:36])(=[O:34])=[O:33])[CH:18]2[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][C:45](Cl)=[O:46].Cl>C(Cl)Cl.N1C=CC=CC=1>[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][C:45]([NH:12][CH:13]1[C:20](=[O:21])[N:19]2[CH:14]1[S:15][CH2:16][N:17]([S:32]([C:35]([F:37])([F:36])[F:38])(=[O:34])=[O:33])[CH:18]2[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])=[O:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 1623622-Thiopheneacetyl chlorideHCID 20429062HCID 20429062, compound

Product 1

HCID 20429034HCID 20429034, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-55 °C

Procedure

To a suspension of p-toluenesulfonic acid salt of benzyl 7-amino-8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (800 mg.) in methylene chloride (8 ml.) was added pyridine (146 μl). After stirring at -55° C. for 5 minutes, 2-(2-thienyl)acetyl chloride (290 mg.) was added thereto, and then the mixture was gradually allowed to warm to 0° C. over a period of 1.5 hours. The mixture was poured into chilled dilute hydrochloric acid and extracted with ethyl acetate (50 ml.). The extract was washed with water (×2), a dilute aqueous solution of sodium bicarbonate, water and an aqueous solution of sodium chloride, successively. Drying over magnesium sulfate and removal of the solvent left an amorphous solid (800 mg.), which was chromatographed on silica gel (10 g.) with a mixed solvent of methylene chloride and ethyl acetate (95:5 to 90:10 by volume) to give benzyl 7-[2-(2-thienyl)acetamido] -8-oxo-3-trifluoromethanesulfonyl-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate (667 mg.).

Workup

  1. temperatureto warm to 0° C. over a period of 1.5 hours
  2. additionThe mixture was poured
  3. extractionextracted with ethyl acetate (50 ml.)
  4. washThe extract was washed with water (×2)
  5. dry with materialDrying over magnesium sulfate and removal of the solvent
  6. waitleft an amorphous solid (800 mg.), which
  7. customwas chromatographed on silica gel (10 g.) with a mixed solvent of methylene chloride and ethyl acetate (95:5 to 90:10 by volume)

Sources & evidence

ORD record
ord-439b24fff9af439198a3e3fc40e76701
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

Loading…