Tert-butyl 4-(2-(4-chloro-2-ureidophenoxy)acetyl)piperidine-1-carboxylate → HCID 68586604, compound

HRID 2189501Notes

Reaction equation

HRID 2189501 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[O:9])=[C:4]([NH:25][C:26]([NH2:28])=[O:27])[CH:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][C:8](=[O:9])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[C:4]([NH:25][C:26]([NH2:28])=[O:27])[CH:3]=1

Participants

4

Reactant 1

HCID 68586517Tert-butyl 4-(2-(4-chloro-2-ureidophenoxy)acetyl)piperidine-1-carboxylate

Product 1

HCID 68586604HCID 68586604, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A sample of tert-butyl 4-(2-(4-chloro-2-ureidophenoxy)acetyl)piperidine-1-carboxylate (264 mg, 0.64 mmol) was dissolved in CH2Cl2 (8 mL) and TFA (4 mL). The resultant homogeneous solution was stirred for 3 h and concentrated in vacuo. The resultant residue was partitioned between EtOAc and sat. NaHCO3. The phases were separated and the aqueous phase was basified to pH˜14 (paper) with 1N NaOH before being extracted with EtOAc (twice). The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 1-(5-chloro-2-(2-oxo-2-(piperidin-4-yl)ethoxy)phenyl)urea. LC/MS [M+H]+=312.07, [M+Na]+=334.04.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was partitioned between EtOAc and sat. NaHCO3
  3. customThe phases were separated
  4. extractionbefore being extracted with EtOAc (twice)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10ee7f36ac8c43f2b38dc6ed460cdaf3
Source dataset
uspto-grants-2012_12
Patent number
US08324251B2

Reaction notes

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