ethyl (RS)-alpha-(sulphonylmethyl)hydrocinnamate guanidine salt → (RS)-alpha-(sulphonylmethyl)hydrocinnamic acid guanidine salt

HRID 2294714Notes

Reaction equation

HRID 2294714 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[S:5](=[CH:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([O:12]CC)=[O:11])(=[O:7])=[O:6]>Cl>[NH2:3][C:2]([NH2:4])=[NH:1].[S:5](=[CH:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([OH:12])=[O:11])(=[O:7])=[O:6]

Participants

3

Reactant 1

HCID 86751650ethyl (RS)-alpha-(sulphonylmethyl)hydrocinnamate guanidine salt

Product 1

HCID 86751649(RS)-alpha-(sulphonylmethyl)hydrocinnamic acid guanidine saltYield 22.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3.11 g (9.4 mmol) of ethyl (RS)-α-(sulphonylmethyl)hydrocinnamate guanidine salt in 400 ml of semi-concentrated hydrochloric acid is heated to reflux for 20 hours. Subsequently, the reaction solution is evaporated under reduced pressure and, for purification, 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. After lyophilization from water there is obtained 0.6 g of (RS)-α-(sulphonylmethyl)hydrocinnamic acid guanidine salt as a colourless powder, MS: 243 (M-H)-.

Workup

  1. temperatureto reflux for 20 hours
  2. customSubsequently, the reaction solution is evaporated under reduced pressure and, for purification
  3. customthe residue obtained
  4. customis chromatographed on 50 g of silica gel using a 9:1
  5. additionto 1:1 mixture of water and methanol as the eluent

Sources & evidence

ORD record
ord-9d9649e1d32241ecb56a48af16fcea30
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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