Bromine → HCID 54404863, compound

HRID 1758698Notes

Reaction equation

HRID 1758698 reaction equation
C[CH:2]1C=C(C2C=CC=CC=2)[O:4][C:3]1=O.CC1C(=O)OC(C2C=CC=CC=2)C=1.[C:27]([CH2:35][CH:36]([CH3:49])[C:37]([N:39]1[CH:43]([C:44]([OH:46])=[O:45])[CH2:42][S:41][C:40]1([CH3:48])[CH3:47])=[O:38])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.BrBr.C([O-])(=S)C.[K+]>C(O)(=O)C.C(O)(C)C.C(N(CC)CC)C>[C:3]([CH:35]([C:27](=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:36]([CH3:49])[C:37]([N:39]1[C@H:43]([C:44]([OH:46])=[O:45])[CH2:42][S:41][C:40]1([CH3:48])[CH3:47])=[O:38])(=[O:4])[CH3:2]

Participants

9

Reactant 5

HCID 24408BromineHCID 113557793-methyl-5-phenyl-2(5H)-furanoneHCID 131044283-Methyl-5-phenylfuran-2(3H)-oneHCID 23670855Potassium ethanethioateHCID 54245864HCID 54245864, compound2×

Product 1

HCID 54404863HCID 54404863, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 8.39 g. (0.052 mole) of L-2,2-dimethylthiazolidine-4-carboxylic acid and 5.26 g. of triethylamine is heated on a steam bath. To the mixture is added 0.052 mole of a mixture of 3-methyl-5-phenyl-2(3H)-furanone and 3-methyl-5-phenyl-2(5H)-furanone in 150 ml. of dry isopropyl alcohol. The mixture is refluxed for 144 hours and the solvent is removed in vacuo. The residue is partitioned between water and ethyl acetate. The aqueous layer is poured onto crushed ice and acidified with hydrochloric acid. The mixture is extracted with ethyl acetate and the organic layer is dried over sodium sulfate. The solvent is removed to give 4.8 g. of a yellow glass which is a mixture of [4R-(4R*,2'R*)]-3-(3-benzoyl-2-methylpropionyl)-2,2-dimethyl-4-thiazolidinecarboxylic acid and [4R-(4R*,2'S*)]-3-(3-benzoyl-2-methylpropionyl)-2,2-dimethyl-4-thiazolidinecarboxylic acid. The mixture is dissolved in acetic acid containing anhydrous hydrogen bromide gas and to the mixture is added bromine. Removal of the solvent gives a glass which is reacted with potassium thioacetate as in the procedure of Example 1 to give the product of the Example as a mixture of diastereomers.

Workup

  1. additionA mixture of 8.39 g
  2. temperatureThe mixture is refluxed for 144 hours
  3. customthe solvent is removed in vacuo
  4. customThe residue is partitioned between water and ethyl acetate
  5. additionThe aqueous layer is poured
  6. customonto crushed ice
  7. extractionThe mixture is extracted with ethyl acetate
  8. dry with materialthe organic layer is dried over sodium sulfate
  9. customThe solvent is removed
  10. customto give 4.8 g
  11. customRemoval of the solvent
  12. customgives a glass which
  13. customto give the product of the Example
  14. additionas a mixture of diastereomers

Sources & evidence

ORD record
ord-12c3bd6fb8c745c399fedbc21d47396d
Source dataset
uspto-grants-1983_02
Patent number
US04374249

Reaction notes

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