Guanidine Hydrochloride → HCID 67028159, compound

HRID 882930Notes

Reaction equation

HRID 882930 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([S:20](Cl)(=[O:22])=[O:21])[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.Cl.[NH2:33][C:34]([NH2:36])=[NH:35]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([S:20](=[O:22])(=[O:21])[N:33]=[C:34]([NH2:36])[NH2:35])[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 8471TriethylamineHCID 86656664HCID 86656664, compound

Product 1

HCID 67028159HCID 67028159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3-chlorosulfonyl-4-methoxy-phenyl)-3-phenyl-propionic acid methyl ester (500 mg, 1.36 mmol) in DCM (50 mL) is added triethylamine (0.57 ml, 4.08 mmol) and guanidine hydrochloride (0.14 g, 1.50 mmol). The reaction mixture is stirred at RT overnight, then diluted with DCM (100 mL). The reaction mixture is washed with an aqueous saturated solution of NaHCO3 (30 mL), water (30 mL) then brine (30 mL). The organic phase is then dried over MgSO4, filtered and concentrated in vacuo. Purification of the residue by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA) affords the title compound.

Workup

  1. washThe reaction mixture is washed with an aqueous saturated solution of NaHCO3 (30 mL), water (30 mL)
  2. dry with materialThe organic phase is then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by reverse phase chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% TFA)

Sources & evidence

ORD record
ord-c3991c33f574494e80f74a7ff6a6bc27
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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