Acetone → HCID 23370048, compound

HRID 1900917Notes

Reaction equation

HRID 1900917 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][CH2:14]2)=[O:12])=[O:9])=[CH:6][CH:5]=1)(=S)[NH2:2].IC.CC(C)=O.C([O-])(=O)C.[NH4+:39]>ClCCl.C(O)C>[C:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][CH2:14]2)=[O:12])=[O:9])=[CH:6][CH:5]=1)(=[NH:39])[NH2:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 517165Ammonium AcetateHCID 23370060HCID 23370060, compound

Product 1

HCID 23370048HCID 23370048, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, the product from step (d) (380 mg), iodomethane (2 ml) and acetone (40 ml) were reacted at ambient temperature and the product so obtained was reacted with ammonium acetate (800 mg), ethanol (40 ml) and dichloromethane (20 ml). This yielded an oily residue which was purified by column chromatography on silica eluting with 10% ethanol/dichloromethane to give ethyl N-[N-(4-amidinobenzoyl)carbamoyl]piperidin-4-ylmethoxyacetate (210 mg) which was used without further purification.

Workup

  1. customthe product so obtained
  2. customThis yielded an oily residue which
  3. customwas purified by column chromatography on silica eluting with 10% ethanol/dichloromethane

Sources & evidence

ORD record
ord-85989030e2dd4a17a2b4421fa28ef8e4
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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