Diisopropylethylamine → 3,5-Dichlorobenzyl 4-(2-(2-oxo-2,3-dihydrooxazole-5-carboxamido)ethyl)piperidine-1-carboxylate

HRID 1480408Notes

Reaction equation

HRID 1480408 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]=[C:4]([C:7]([NH:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:8])[O:3]1.CCN(C(C)C)C(C)C.[C:27](Cl)(=[O:38])[O:28][CH2:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1>C(Cl)Cl>[O:1]=[C:2]1[NH:6][CH:5]=[C:4]([C:7]([NH:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([C:27]([O:28][CH2:29][C:30]3[CH:31]=[C:32]([Cl:37])[CH:33]=[C:34]([Cl:36])[CH:35]=3)=[O:38])[CH2:14][CH2:13]2)=[O:8])[O:3]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 867226442-oxo-N-(2-(piperidin-4-yl)ethyl)-2,3-dihydrooxazole-5-carboxamide

Product 1

HCID 762841533,5-Dichlorobenzyl 4-(2-(2-oxo-2,3-dihydrooxazole-5-carboxamido)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-oxo-N-(2-(piperidin-4-yl)ethyl)-2,3-dihydrooxazole-5-carboxamide (step 3) (210 mg, 0.76 mmol) was suspended in DCM (2 ml). DIPEA (265 μl, 1.52 mmol) was added and the reaction mixture sonicated to aid dissolution. 3,5-dichlorobenzyl carbonochloridate (182 mg, 0.76 mmol) in DCM (2 ml) was added and the mixture was left stirring vigorously at RT overnight. The resulting mixture was diluted with DCM and washed with citric acid (emulsion formed). Brine was added and organics were separated, dried over MgSO4 (anh), filtered and evaporated under reduced pressure. The crude product was purified by chromatography on silica eluting with 75-100% EtOAc in iso-hexane to afford the title compound;

Workup

  1. customthe reaction mixture sonicated
  2. dissolutiondissolution
  3. waitthe mixture was left
  4. washwashed with citric acid (emulsion formed)
  5. additionBrine was added
  6. customorganics were separated
  7. dry with materialdried over MgSO4 (anh)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude product was purified by chromatography on silica eluting with 75-100% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-4732571d22c84ab5b981e2b72accf06d
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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