Cesium carbonate → HCID 22184797, compound

HRID 890387Notes

Reaction equation

HRID 890387 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH2:14]Cl)=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[CH2:23]([O:25][C:26](=[O:29])[CH2:27][NH2:28])[CH3:24]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH2:14][NH:28][CH2:27][C:26]([O:25][CH2:23][CH3:24])=[O:29])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2063649HCID 2063649, compoundHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 22184797HCID 22184797, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-ethoxycarbonyl-4-chloromethylcarbonylpiperazine (520 mg, 2.21 mmol) in DMF (40 mL) was added cesium carbonate (2.0 g, 6.20 mmol) and glycine ethyl ester hydrochloride (310 mg, 2.21 mmol). The resulting reaction mixture was stirred at 50° C. After 1 hour, the reaction mixture was diluted with ethyl acetate (200 mL), washed with water (3×150 mL) and brine, and concentrated in vacuo to afford 1-ethoxycarbonyl-4-(ethoxycarbonylmethyl)aminomethylcarbonylpiperazine as an oil (520 mg), which was used without purification.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water (3×150 mL) and brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a094e0d3b4724f44bfbddda00a4b6790
Source dataset
uspto-grants-2006_02
Patent number
US06995156B2

Reaction notes

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