Carbonic acid di-2-pyridyl ester → 1-Amino-3,3-diethoxypropane

HRID 1351825Notes

Reaction equation

HRID 1351825 reaction equation
FC1C(OC(=O)CCC[CH2:13][CH2:14][N:15]2C(=O)C=CC2=O)=C(F)C(F)=C(F)C=1F.[C:27](=O)([O:35][C:36]1[CH:41]=CC=CN=1)[O:28][C:29]1[CH:34]=CC=CN=1>C(Cl)Cl>[NH2:15][CH2:14][CH2:13][CH:27]([O:28][CH2:29][CH3:34])[O:35][CH2:36][CH3:41]

Participants

4

Reactant 2

HCID 2757370Carbonic acid di-2-pyridyl esterHCID 16655880HCID 16655880, compound

Product 1

HCID 5210291-Amino-3,3-diethoxypropane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 924 mg (3 mmol) of 6-maleimidocaproic acid pentafluorophenyl ester 1 (see Example 11) dissolved in dry methylene chloride (30 ml) was added 10 g (1 mmol) of alpha-amino-omega-carboxy-PEG (2) (MW 10,000, n=226) and 4-dimethylpyridine (402 mg, 3 mmol) dissolved in 50 ml of dry methylene chloride. The reaction mixture was stirred at room temperature for 2 h and the product precipitated in ether (100 ml). After cooling to 4° C. the crude amide of formula 3 was collected by filtration and precipitated twice from methylene chloride by addition of ether to give 9 g of compound 3 as a white solid.

Workup

  1. customthe product precipitated in ether (100 ml)
  2. temperatureAfter cooling to 4° C. the crude amide of formula 3
  3. filtrationwas collected by filtration
  4. customprecipitated twice from methylene chloride by addition of ether

Sources & evidence

ORD record
ord-0ef7f3be60274a1b8e6d28963d1983cc
Source dataset
uspto-grants-2007_05
Patent number
US07217845B2

Reaction notes

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