Diethyl Ether → Ethyl 2-(tert-butyl(hex-5-ynyl)amino)-2-oxoacetate

HRID 1971723Notes

Reaction equation

HRID 1971723 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:17][CH3:18])CC)C.CC[C:21]([C:23](Cl)=[O:24])=[O:22].C([O:28]CC)C>>[C:1]([N:5]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11])[C:23](=[O:24])[C:21]([O:28][CH2:17][CH3:18])=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 11007880Butanoyl chloride, 2-oxo-HCID 58124927N-tert-butylhex-5-yn-1-amine

Product 1

HCID 58124820Ethyl 2-(tert-butyl(hex-5-ynyl)amino)-2-oxoacetate

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g of 17c in 10 ml of diethyl ether was added 1.5 ml of triethyl amine, followed, at 0° C., by 0.8 ml of ethyloxalyl chloride. The mixture was stirred for 1/2 hr at 0° C. and then poured into 30 ml of ice water and extracted with diethyl ether. The organic layer was washed with 1N NaOH, 1N HCl, water, dried and concentrated, to give 1.2 g of 17d as an oil. Rf 0.15 (heptane/ethyl acetate 9/1).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with 1N NaOH, 1N HCl, water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f5c48039461b4754b10cfea3f678acf7
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…