Carbonic acid-guanidine (1:1) → ethyl (RS)-alpha-(sulphonylmethyl)hydrocinnamate guanidine salt

HRID 2294713Notes

Reaction equation

HRID 2294713 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[CH2:9]([CH:16]([CH2:22][S:23](Cl)(=[O:25])=[O:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)Cl.CN(C)C=O>[NH2:7][C:6]([NH2:8])=[NH:5].[S:23](=[CH:22][CH:16]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 21475177Ethyl 2-benzyl-3-chlorosulphonylpropionate

Product 1

HCID 86751650ethyl (RS)-alpha-(sulphonylmethyl)hydrocinnamate guanidine saltYield 64.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5.06 g (28 mmol) of guanidine carbonate are added at -10° to a solution of 4.73 g (16.2 mmol) of crude ethyl 2-benzyl-3-chlorosulphonyl-propionate, prepared according to the procedure described in EPA 0236734, in 150 ml of methylene chloride and 40 ml of dimethylformamide. The reaction mixture is stirred at room temperature overnight and thereafter evaporated. The residue is partitioned between methylene chloride and water, the aqueous phase is separated, evaporated under reduced pressure and the residue obtained is chromatographed on 50 g of silica gel using a 9:1 to 1:1 mixture of water and methanol as the eluent. The product obtained is recrystallized from a mixture of methanol and ether. There are obtained 3.29 g of ethyl (RS)-α-(sulphonylmethyl)hydrocinnamate guanidine salt as colourless crystals.

Workup

  1. customprepared
  2. customevaporated
  3. customThe residue is partitioned between methylene chloride and water
  4. customthe aqueous phase is separated
  5. customevaporated under reduced pressure
  6. customthe residue obtained
  7. customis chromatographed on 50 g of silica gel using a 9:1
  8. additionto 1:1 mixture of water and methanol as the eluent
  9. customThe product obtained
  10. customis recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-76fa7e3068cf4f9687469e4b291bea3b
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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