Putrescine → HCID 86672881, compound

HRID 1616955Notes

Reaction equation

HRID 1616955 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[C:8]([O:10]CC)=O>C(O)C>[CH2:15]([O:14][C:7](=[O:13])[C:8]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:8](=[O:10])[C:7]([OH:14])=[O:13])=[O:10])[CH3:16]

Participants

4

Reactant 2

HCID 1045PutrescineHCID 7268Diethyl Oxalate

Product 1

HCID 86672881HCID 86672881, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1,4-diaminobutane (88.2 grams) in 100 mL ethanol was added to ice cooled diethyl oxalate (1461 grams) in ethanol (1400 mL) over 40 minutes, maintaining the internal temperature below 8° C. The reaction was allowed to gradually warm to ambient temperature, and after 48 hours, the crude solids (168 grams) were collected by filtration. The product (22 grams) was purified by flash column chromatography (EtOAc as the eluent) and then boiled in MTBE (200 mL) to obtain butylene-bis-oxamic acid ethyl ester as a white solid having a melting point in the range of 114.4 to 116.4° C. 1H NMR (CDCl3, 300 MHz) δ 7.23 (brs, 2H), 4.33 (q, J=7.1 Hz, 4H), 3.36 (q, J=6.5 Hz, 4H), 1.64-1.59 (m, 4H), 1.36 (t, J=7.2 Hz, 6H).

Workup

  1. temperaturemaintaining the internal temperature below 8° C
  2. filtrationthe crude solids (168 grams) were collected by filtration
  3. customThe product (22 grams) was purified by flash column chromatography (EtOAc as the eluent) and

Sources & evidence

ORD record
ord-017819ab20f144e3bbe34ff686ac349a
Source dataset
uspto-grants-2014_07
Patent number
US08765881B2

Reaction notes

Loading…