Triethylamine → HCID 70093230, compound

HRID 1085048Notes

Reaction equation

HRID 1085048 reaction equation
[C:1]([CH2:5][CH2:6][C:7](Cl)=[O:8])([O:3]C)=[O:2].[OH:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].[CH2:18](N(CC)CC)C>C(OCC)(=O)C>[C:7]([OH:8])(=[O:10])[CH2:6][CH2:5][C:1]([OH:3])=[O:2].[CH3:18][CH:13]1[CH2:14][C:15](=[O:16])[NH:11][C:12]1=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 80170N-Hydroxysuccinimide

Product 1

HCID 70093230HCID 70093230, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-carbomethoxypropionyl chloride (5 g, 33.2 mmoles) and N-hydroxysuccinimide (3.8 g, 33.2 mmoles) in ethyl acetate (60 ml) was cooled to 5° C. While stirring, triethylamine (4.3 g, 33.2 mmoles) was slowly added to the cooled solution over a 15 min interval. The mixture was allowed to equilibrate to room temperature (22° C.) and react for an additional 3 h. The formed triethylamine salt was filtered, washed with ethyl acetate and the filtrate evaporated under vacuum. The powder was recrystallized from ethyl acetate/hexane to give 5.5 g (24.2 mmoles) (72% yield) of white needles mp 84°-86° C.). 1H-NMR (CDCl3) δ 2.44(2Ha,app.t, J=8Hz); 2.64(2Ha',app.t, J=8Hz); 2.86 (4Hb,s); 3.66(3Hc,s)ppm. IR (Nujol) 1840, 1800, 1775, 1725 cm-1`.

Workup

  1. customto equilibrate to room temperature
  2. custom(22° C.)
  3. customreact for an additional 3 h
  4. filtrationThe formed triethylamine salt was filtered
  5. washwashed with ethyl acetate
  6. customthe filtrate evaporated under vacuum
  7. customThe powder was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-45f61be54a57487999ccc777a01f591a
Source dataset
uspto-grants-1991_04
Patent number
US05008245

Reaction notes

Loading…