Guanidine Hydrochloride → HCID 178505333, compound

HRID 1582227Notes

Reaction equation

HRID 1582227 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].C([O:12][C@@H:13]1[C@@H:34]([O:35]C(=O)C)[C@H:33]([O:39]C(=O)C)[C@@H:32]([C:43]([OH:45])=[O:44])[O:31][C@H:14]1[O:15][C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[C:21]([C:26](OCC)=[O:27])[N:22]2[CH3:25])=[CH:18][CH:17]=1)(=O)C.[CH3:46][S:47]([OH:50])(=[O:49])=[O:48]>CN(C)C=O.O.C1(C)C=CC=CC=1>[CH3:46][S:47]([OH:50])(=[O:49])=[O:48].[O:15]([C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[C:21]([C:26]([NH:4][C:3]([NH2:5])=[NH:2])=[O:27])[N:22]2[CH3:25])=[CH:18][CH:17]=1)[C@@H:14]1[O:31][C@H:32]([C:43]([OH:45])=[O:44])[C@@H:33]([OH:39])[C@H:34]([OH:35])[C@H:13]1[OH:12]

Participants

8

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 6395Methanesulfonic AcidHCID 10942334Sodium MethoxideHCID 20725743HCID 20725743, compound

Product 1

HCID 178505333HCID 178505333, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

Guanidine hydrochloride (6.23 g, 65.2 mmol) was added to a mixture of sodium methoxide (3.52 g, 65.2 mmol) and N,N-dimethylformamide (25 ml), and the resulting mixture was stirred at room temperature for 1 hour. The solid precipitated was filtered off and a solution of (2-ethoxycarbonyl-1-methyl-1H-indol-6-yl) 2,3,4-tri-O-acetyl-β-D-glucopyranosideuronic acid (1.70 g, 3.26 mmol) in N,N-dimethylformamide (9 ml) was added to the filtrate obtained, followed by stirring at room temperature for 7 hours. After toluene was added to the reaction mixture, the resulting mixture was concentrated under reduced pressure, and the resulting residue was purified by a reversed phase column chromatography (eluent; water:methanol=9:1) to obtain a free compound. The free compound was dissolved in water (50 ml) and methanesulfonic acid (1.15 g) was added thereto under ice-cooling. Subsequently, the solvent was distilled off under reduced pressure and the resulting residue was washed with tetrahydrofuran to obtain 0.78 g of [2-[[[amino(imino)methyl]amino]carbonyl]-1-methyl-1H-indol-6-yl] β-D-glucopyranosideuronic acid methanesulfonate.

Workup

  1. customThe solid precipitated
  2. filtrationwas filtered off
  3. customobtained
  4. stirringby stirring at room temperature for 7 hours
  5. concentrationthe resulting mixture was concentrated under reduced pressure
  6. customthe resulting residue was purified by a reversed phase column chromatography (eluent; water:methanol=9:1)
  7. customto obtain a free compound
  8. temperatureunder ice-cooling
  9. distillationSubsequently, the solvent was distilled off under reduced pressure
  10. washthe resulting residue was washed with tetrahydrofuran

Sources & evidence

ORD record
ord-b974a70f68db42eba22f4ac2597b217d
Source dataset
uspto-grants-2004_05
Patent number
US06734205B2

Reaction notes

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