Water → HCID 178471702, compound

HRID 1976296Notes

Reaction equation

HRID 1976296 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:42]=[CH:41][C:13]([C:14]([NH:16][S:17]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([O:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]CC(Cl)(Cl)Cl)=[O:32])=[C:22]([CH3:39])[C:21]=2[CH3:40])(=[O:19])=[O:18])=[NH:15])=[CH:12][CH:11]=1)=[O:5])[CH3:2].O>[Zn].CC(O)=O>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:42]=[CH:41][C:13]([C:14]([NH:16][S:17]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([O:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[C:22]([CH3:39])[C:21]=2[CH3:40])(=[O:19])=[O:18])=[NH:15])=[CH:12][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 178471703HCID 178471703, compound

Product 1

HCID 178471702HCID 178471702, compoundYield 32.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zn powder (0.32 g) was added to a mixture of 4-ethoxycarbonylpropoxy-N-{4-[3-(2,2,2-trichloroethoxycarbonyl)propoxy]-2,3,6-trimethylbenzenesulfonyl}benzamidine (0.65 g), water (2 ml), and AcOH (18 ml) under ice-water cooling. The reaction mixture was stirred at room temperature for 3.25 hours, and then evaporated. The resulting precipitate was removed by filtration, and was washed with AcOEt and isopropyl ether (IPE). The filtrate, AcOEt, and IPE were combined, and then washed with water. The organic phase was dried over MgSO4, and evaporated. The resulting residue was purified by chromatography over silica gel (CHCl3-MeOH as eluent) to give 4-ethoxycarbonylpropoxy-N-[4-(3-carboxypropoxy)-2,3,6-trimethylbenzenesulfonyl]benzamidine (0.17 g) as an oil compound.

Workup

  1. customevaporated
  2. customThe resulting precipitate was removed by filtration
  3. washwas washed with AcOEt and isopropyl ether (IPE)
  4. washwashed with water
  5. dry with materialThe organic phase was dried over MgSO4
  6. customevaporated
  7. customThe resulting residue was purified by chromatography over silica gel (CHCl3-MeOH as eluent)

Sources & evidence

ORD record
ord-b16f72b96a2543859bdb22ec77f15d3f
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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