Hydrochloric Acid → HCID 86739990, compound

HRID 2164592Notes

Reaction equation

HRID 2164592 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH2:19][CH:18]3[CH:15]([C:16](OC)([O:20]C)[CH2:17]3)[C:14]=2[C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl>C(Cl)Cl.C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([C:13]2[CH2:19][CH:18]3[CH:15]([C:16](=[O:20])[CH2:17]3)[C:14]=2[C:24]([O:26][CH:27]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])(=[O:12])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86739991HCID 86739991, compound

Product 1

HCID 86739990HCID 86739990, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg of 3-(p-nitrophenylsulfonyl)-7,7-dimethoxybicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenylmethyl ester, in 5 mL of methylene chloride was diluted with 20 mL of acetic acid. Aqueous hydrochloric acid (4N, 3 mL) was added, the mixture was stirred for 1 hr at room temperature, and then evaporated to dryness at 25°. The residue was partitioned between methylene chloride and water and the organic layer was washed with brine, dried (Na2SO4), and evaporated. The residue was dissolved in a small amount of 5% methanol in methylene chloride and treated with an excess of diphenyldiazomethane to esterify any free acid present. After nitrogen evolution ceased, the reaction mixture was evaporated to dryness and the residue was dissolved in methylene chloride-ether to give a solution from which precipitated 127 mg (69.3%) of 3-(p-nitrophenylsulfonyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenyl methyl ester, as colorless crystals. IR (Nujol mull): 1730, 1780 cm-1 ; NMR (80 MHz; CDCl3): δ 2.5-3.6 (5H, m), 4.7 (1H, m), 7.0 (1H, s), 7.2-7.5 (10H, m), 8.0 (2H, d, J=9), and 8.23 (2H, d, J=9). ##STR26##

Workup

  1. customevaporated to dryness at 25°
  2. customThe residue was partitioned between methylene chloride and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in a small amount of 5% methanol in methylene chloride
  7. additiontreated with an excess of diphenyldiazomethane
  8. customthe reaction mixture was evaporated to dryness
  9. dissolutionthe residue was dissolved in methylene chloride-ether
  10. customto give a solution from which
  11. customprecipitated 127 mg (69.3%) of 3-(p-nitrophenylsulfonyl)-7-oxobicyclo[3.2.0]hept-2-en-2-carboxylic acid, diphenyl methyl ester

Sources & evidence

ORD record
ord-6a52231f7c8a46d097454f5661663d53
Source dataset
uspto-grants-1985_03
Patent number
US04505905

Reaction notes

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