Diisopropylethylamine → ethyl (Z)-3-[(3-ethoxy-3-oxo-propanoyl)amino]-2-ethyl-but-2-enoate

HRID 1508685Notes

Reaction equation

HRID 1508685 reaction equation
[NH2:1]/[C:2](/[CH3:11])=[C:3](/[CH2:9][CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(C(C)C)CC)(C)C.Cl[C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:22]([NH:1]/[C:2](/[CH3:11])=[C:3](/[CH2:9][CH3:10])\[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 10630766Ethyl 3-amino-2-ethylcrotonate

Product 1

HCID 90338651ethyl (Z)-3-[(3-ethoxy-3-oxo-propanoyl)amino]-2-ethyl-but-2-enoateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100-mL round bottom flask was charged with ethyl (Z)-3-amino-2-ethyl-but-2-enoate (880 mg, 5.6 mmol, 1 eq.), diisopropylethylamine (750 mg, 5.8 mmol, 1.04 eq.) and THF (10 ml). To the mixture was added ethyl 3-chloro-3-oxo-propanoate (840 mg, 5.6 mmol, 1 eq.) dropwise by a syringe at 0° C. After the addition was complete, the resulting mixture was stirred at room temperature overnight and then added to aqueous sodium bicarbonate solution. The mixture was extracted with ethyl acetate (3×15 ml). The combined organic layer was dried over anhydrous Na2SO4. Removal of solvent gave the crude product ethyl (Z)-3-[(3-ethoxy-3-oxo-propanoyl)amino]-2-ethyl-but-2-enoate as yellow oil (1.3 g, 86% yield).

Workup

  1. additionAfter the addition
  2. extractionThe mixture was extracted with ethyl acetate (3×15 ml)
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-a74534801015490d81c44b2f43e486d4
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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