HCID 86743775, compound → HCID 13986801, compound

HRID 1200143Notes

Reaction equation

HRID 1200143 reaction equation
[C:1]([N:9]1[C@H:13]([C:14]([O-:16])=[O:15])[CH2:12][S@:11](=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([NH2+]C2CCCCC2)CCCCC1>C(O)C>[C:1]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][S@:11](=[O:17])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 86743775HCID 86743775, compound

Product 1

HCID 13986801HCID 13986801, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the alcoholic mother liquor, from which fractional recrystallization had been effected in step (c), a small excess of dicyclohexylamine was added, and then the mixture was allowed to stand at room temperature for 2 hours. The crystals which precipitated were recrystallized from ethanol to give 3.95 g of dicyclohexylammonium (1S,4R)-3-benzoyl-1-oxothiazolidine-4-carboxylate, melting at 186°-198° C. (with decomposition). 3.0 g of the cyclohexyl amine salt thus obtained were dissolved in 50 ml of 50% v/v aqueous ethanol, and the solution was passed through a column containing 50 ml of a cation-exchange resin (Dowex 50H+, trade mark), and eluted with 50% v/v aqueous ethanol. The solvent was distilled off and the residue was recrystallized from a 1:3 by volume mixture of ethanol and diethyl ether, to give 1.54 g of (1S,4R)-3-benzoyl-1-oxothiazolidine-4-carboxylic acid melting at 174°-175° C. (with decomposition).

Workup

  1. washeluted with 50% v/v aqueous ethanol
  2. distillationThe solvent was distilled off
  3. customthe residue was recrystallized from a 1:3 by volume mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-9cfeff81db9f4e2da406345e880e9de1
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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