Methanol → 3-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-3-oxopropionic acid

HRID 2120885Notes

Reaction equation

HRID 2120885 reaction equation
C[O:2][C:3](=[O:20])[CH2:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)=[O:6].O.CO.[Cl-].[Li+]>O1CCCC1>[C:16]([O:15][C:13]([N:10]1[CH2:9][CH2:8][N:7]([C:5](=[O:6])[CH2:4][C:3]([OH:20])=[O:2])[CH2:12][CH2:11]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 433294Lithium ChlorideHCID 206224123-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-3-oxopropionic acid methyl ester

Product 1

HCID 234354453-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-3-oxopropionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-3-oxopropionic acid methyl ester (35) (3.30 g; 11.5 mmol) is dissolved in 2:2:2 tetrahydrofuran: water: methanol. Lithium chloride (2.76 g; 115.3 mmol) is added and the mixture is stirred for 1 hour at ambient temperature. The solution is concentrated in vacuo to remove the tetrahydrofuran and methanol. The concentrate is poured onto citric acid solution (115 mL) and extracted with ethyl acetate (230 mL). The organic layer is washed with water (3×115 mL) and brine (1×115 mL), then dried over magnesium sulfate, filtered and concentrated in vacuo to afford the desired product as a solid. ESMS: MH+ 273.0

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. customto remove the tetrahydrofuran and methanol
  3. additionThe concentrate is poured onto citric acid solution (115 mL)
  4. extractionextracted with ethyl acetate (230 mL)
  5. washThe organic layer is washed with water (3×115 mL) and brine (1×115 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4c5037617d64b2397f3f69aa82b2c76
Source dataset
uspto-grants-2004_02
Patent number
US06693099B2

Reaction notes

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