Hydrochloric Acid → 3,5-Dichlorobenzyl 4-(2-((2-hydroxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)piperidine-1-carboxylate

HRID 1480368Notes

Reaction equation

HRID 1480368 reaction equation
C([O:3][C:4]1[C:7](=[O:8])[C:6](=[O:9])[C:5]=1[NH:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)=[O:20])[CH2:15][CH2:14]1)C.Cl>C1COCC1>[OH:9][C:6]1[C:7](=[O:8])[C:4](=[O:3])[C:5]=1[NH:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)=[O:20])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 762841493,5-Dichlorobenzyl 4-(2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)piperidine-1-carboxylate

Product 1

HCID 902188003,5-Dichlorobenzyl 4-(2-((2-hydroxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 3,5-dichlorobenzyl 4-(2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)ethyl)piperidine-1-carboxylate (Example 3) (35 mg, 0.077 mmol) and 6M HCl (aq) (38.4 μl, 0.077 mmol) in THF (256 μl) was stirred overnight at room temperature. The reaction mixture was concentrated under pressure to give an aqueous suspension. The suspension was filtered, air dried and partitioned between EtOAc and water. The organic portion was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Further purification was carried out using preparative LC-MS. The resulting product fractions were concentrated under reduced pressure to give an aqueous solution and then extracted with EtOAc. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under pressure
  2. customto give an aqueous suspension
  3. filtrationThe suspension was filtered
  4. customair dried
  5. custompartitioned between EtOAc and water
  6. customThe organic portion was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customFurther purification
  11. concentrationThe resulting product fractions were concentrated under reduced pressure
  12. customto give an aqueous solution
  13. extractionextracted with EtOAc
  14. dry with materialThe organic extracts were dried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-792c73767445484185e60365c09327fb
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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