Dimethyl Sulfoxide → Tert-butyl 4-((4-(methoxycarbonyl)oxazol-2-yl)methyl)piperazine-1-carboxylate

HRID 408844Notes

Reaction equation

HRID 408844 reaction equation
CS(C)=O.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)C(C)C)(C)C.[CH3:27][O:28][C:29]([C:31]1[N:35]=[C:34]([CH2:36]Cl)[O:33][CH:32]=1)=[O:30]>C(OCC)(=O)C>[CH3:27][O:28][C:29]([C:31]1[N:35]=[C:34]([CH2:36][N:15]2[CH2:16][CH2:17][N:12]([C:10]([O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[O:11])[CH2:13][CH2:14]2)[O:33][CH:32]=1)=[O:30]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylate

Product 1

HCID 66661475Tert-butyl 4-((4-(methoxycarbonyl)oxazol-2-yl)methyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A dimethyl sulfoxide (10 mL) solution of tert-butyl-1-piperazine carboxylate (1.06 g, 5.70 mmol) and N,N-diisopropylethylamine (2.98 mL, 17.1 mmol) was treated at room temperature with methyl (2-chloromethyl)oxazole-4-carboxylate (1.0 g, 5.70 mmol; portion-wise addition) and stirred overnight. The mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride. The organic layer was dried on magnesium sulfate, filtered and concentrated to give the intermediate tert-butyl 4-((4-(methoxycarbonyl)oxazol-2-yl)methyl)piperazine-1-carboxylate (MS (ESI) m/z 325.7 [M+H]+. The intermediate was dissolved in dichloromethane (15 mL) at room temperature and treated with trifluoroacetic acid (5 mL) dropwise. The mixture was stirred for 4 hours and was then concentrated under vacuum to give the title compound (1.60 g). MS (ESI) m/z 226.1 [M+H]+.

Workup

  1. washwashed with saturated aqueous sodium chloride
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6fdef101e8ab49689f5f5ac919ce3eb1
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…