Triethylamine → 3,5-Dichlorobenzyl 2-(2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)morpholine-4-carboxylate

HRID 1480382Notes

Reaction equation

HRID 1480382 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.C(N(CC)CC)C.[NH2:20][CH2:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][N:25]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=2)=[O:30])[CH2:24]1>CCO>[CH2:9]([O:8][C:7]1[C:6](=[O:11])[C:5](=[O:12])[C:4]=1[NH:20][CH2:21][CH2:22][CH:23]1[O:28][CH2:27][CH2:26][N:25]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[C:35]([Cl:40])[CH:34]=2)=[O:30])[CH2:24]1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123228Diethyl squarateHCID 867226353,5-Dichlorobenzyl 2-(2-aminoethyl)morpholine-4-carboxylate

Product 1

HCID 762861963,5-Dichlorobenzyl 2-(2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising of 3,4-diethoxycyclobut-3-ene-1,2-dione (77 mg, 0.453 mmol) and triethylamine (253 μl, 1.813 mmol) in EtOH (1511 μl) was stirred at 40° C. for 20 minutes under nitrogen. After cooling to room temperature, 3,5-dichlorobenzyl 2-(2-aminoethyl)morpholine-4-carboxylate (step 2) (151 mg, 0.453 mmol) was added dropwise and the reaction mixture was allowed to stir at room temperature for a further 30 minutes. The resulting reaction mixture was concentrated under reduced pressure and diluted with EtOAc. The organic portion was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was dried loaded using silica onto an ISCO 4 g column, eluting with 0-100% EtOAc in iso-hexane. The product fractions were concentrated under reduced pressure to afford the title compound;

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. washThe organic portion was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dry with materialThe crude material was dried
  9. washeluting with 0-100% EtOAc in iso-hexane
  10. concentrationThe product fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-953eb2ba05664593a1420a5536efc6bb
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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