Triethylamine → ethyl 3-[ethoxycarbonyl-(2-ethoxy-2-oxoethyl)amino]propanoate

HRID 659044Notes

Reaction equation

HRID 659044 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].[CH2:14](N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]([CH2:14][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12887440HCID 12887440, compound

Product 1

HCID 4381617ethyl 3-[ethoxycarbonyl-(2-ethoxy-2-oxoethyl)amino]propanoateYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude intermediate (c) (418 mmol) was dissolved in CH2Cl2 (275 mL) and triethylamine (58.3 mL, 418 mmol) was added followed by ethyl chloroformate (d) (39.8 mL, 418 mmol). The reaction was stirred at ambient temperature for about 24 h. After the reaction was complete, the volatile components were removed under vacuum. The crude product was then distilled under vacuum (about 5 mm Hg) and dissolved in EtOAc which was washed with aqueous saturated KHSO4×3, with brine×1 and dried over Na2SO4. Following filtration, the volatile components were removed under vacuum to afford intermediate (e) as a clear oil (74.8 g, 272 mmol) in 65% yield over two steps.

Workup

  1. customthe volatile components were removed under vacuum
  2. distillationThe crude product was then distilled under vacuum (about 5 mm Hg)
  3. dissolutiondissolved in EtOAc which
  4. washwas washed with aqueous saturated KHSO4×3, with brine×1
  5. dry with materialdried over Na2SO4
  6. filtrationfiltration
  7. customthe volatile components were removed under vacuum

Sources & evidence

ORD record
ord-458e5b3470394c35befca18d4ab875ad
Source dataset
uspto-grants-2011_12
Patent number
US08080556B2

Reaction notes

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