Acetate → 2-(2-Guanidinoethoxy)ethyl acetate

HRID 635553

Reaction equation

HRID 635553 reaction equation
C(O)(=O)C[CH2:3][C:4]([OH:6])=[O:5].O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17].C(OC(=O)C)(=O)C.C([O-])(=O)C>C(N(CC)CC)C>[C:4]([O:6][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([NH2:18])=[NH:17])(=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 175AcetateHCID 7918Acetic AnhydrideHCID 178418465HCID 178418465, compound

Product 1

HCID 1784182412-(2-Guanidinoethoxy)ethyl acetateYield 40%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.06 g (9.99 mmol) of 2-(2-hydroxyethoxy)ethylguanidine succinate, 8 ml of triethylamine, 0.122 mg (1.0 mmol) of 4-N,N-dimethylaminopyridine and 1.02 g (9.99 mmol) of acetic anhydride were placed in a 50 ml two neck flask and were stirred for 1 hour at room temperature. After the upper phase was removed by decantation, the obtained crude product was washed five times with 50 ml of diethylether. The product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid) to obtain 1.00 g of the title compound (starch syrup-like, 4.0 mmol, 40.0% in yield) in the form of acetate. Results of the analysis of this compound are as follows.

Workup

  1. customAfter the upper phase was removed by decantation
  2. customthe obtained crude product
  3. washwas washed five times with 50 ml of diethylether
  4. customThe product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid)

Sources & evidence

ORD record
ord-605fdc7c832c43279cd877d18b16064c
Source dataset
uspto-grants-2001_02
Patent number
US06187955B1

Linked notes

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