Diethyl Ether → Ethyl 2-(tert-butyl(3-(prop-2-ynyloxy)propyl)amino)-2-oxoacetate

HRID 1971657Notes

Reaction equation

HRID 1971657 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][C:11]#[CH:12])([CH3:4])([CH3:3])[CH3:2].C(N([CH2:18][CH3:19])CC)C.CC[C:22]([C:24](Cl)=[O:25])=[O:23].C([O:29]CC)C>>[C:1]([N:5]([CH2:6][CH2:7][CH2:8][O:9][CH2:10][C:11]#[CH:12])[C:24](=[O:25])[C:22]([O:29][CH2:18][CH3:19])=[O:23])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 11007880Butanoyl chloride, 2-oxo-HCID 58124800N-tert-butyl-3-(prop-2-ynyloxy)propan-1-amine

Product 1

HCID 58124912Ethyl 2-(tert-butyl(3-(prop-2-ynyloxy)propyl)amino)-2-oxoacetate

Procedure

To a solution of 750 mg of 7e and 1 ml of triethyl amine in 10 ml of diethyl ether was added, at 0° C., a solution of 0.55 ml of ethyloxalyl chloride in 3 ml of diethyl ether. The mixture was stirred for 15 min and then quenched with 30 ml of water and was extracted with ethyl acetate. The organic layer was washed once with 1M aq. K2CO3 and once with water, dried, concentrated and chromatographed, to provide 1.0 g of 7f as an oil. Rf (heptane/ethyl acetate 1/1) 0.6.

Workup

  1. customquenched with 30 ml of water
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed once with 1M aq. K2CO3 and once with water
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-bb13d2c6855b49379de9740cdff79142
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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