Diethyl Ether → Ethyl 2-((2-(tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl)(isopropyl)amino)-2-oxoacetate

HRID 1971676Notes

Reaction equation

HRID 1971676 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][N:7]([CH2:15][C:16]#[CH:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:3])[CH3:2].C(N([CH2:23][CH3:24])CC)C.CC[C:27]([C:29](Cl)=[O:30])=[O:28].CC[O:34]CC>>[C:10]([O:9][C:8]([N:7]([CH2:15][C:16]#[CH:17])[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[C:29](=[O:30])[C:27]([O:34][CH2:23][CH3:24])=[O:28])=[O:14])([CH3:12])([CH3:11])[CH3:13]

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 11007880Butanoyl chloride, 2-oxo-HCID 58124856Tert-butyl 2-(isopropylamino)ethyl(prop-2-ynyl)carbamate

Product 1

HCID 58124862Ethyl 2-((2-(tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl)(isopropyl)amino)-2-oxoacetate

Procedure

To a solution of 900 mg of 10f and 1 ml of triethyl amine in 10 ml of ether was added at 0° C. a solution of 500 μl of ethyloxalyl chloride in 5 ml of ether. The reaction mixture was stirred for ½ h and then quenched by addition of 5% aq. NH4Cl and extracted with ethyl acetate. The organic layers were combined and washed with 1M K2CO3 and water, dried and concentrated, to give 1.03 g of 10g as an oil.

Workup

  1. customquenched by addition of 5% aq. NH4Cl
  2. extractionextracted with ethyl acetate
  3. washwashed with 1M K2CO3 and water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-afc95efe5f61413591957044f617a8de
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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