Potassium Carbonate → (RS)-3-[2-(4-Fluorophenyl)-2-oxo-ethoxycarbonylmethyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 549350Notes

Reaction equation

HRID 549350 reaction equation
C1C2C(COC([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]3[CH2:31][C:32]([OH:34])=[O:33])=O)C3C(=CC=CC=3)C=2C=CC=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=1)=[O:44]>CN(C=O)C>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][NH:18][CH:19]([CH2:31][C:32]([O:34][CH2:42][C:43]([C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)=[O:44])=[O:33])[CH2:20]1)=[O:25])([CH3:28])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 27567961-Fmoc-4-Boc-Piperazine-2-acetic acid

Product 1

HCID 67158269(RS)-3-[2-(4-Fluorophenyl)-2-oxo-ethoxycarbonylmethyl]piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(RS)-2-Carboxymethylpiperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(9H-fluoren-9-ylmethyl) ester from description 109 (2.0 g) was dissolved in DMF (25 ml) and stirred at room temperature under argon for 3 days in the presence of potassium carbonate (0.697 g) and 2-bromo-4′-fluoroacetophenone (0.930 g). The reaction solution was then partitioned between ethyl acetate and water. the organic solution was washed with brine, dried (MgSO4) and evaporated. The crude product was chromatographed over silica gel, eluting with 25 to 100% ethyl acetate in hexane, followed by 10% ethanol in ethyl acetate. The title compound was obtained as a pale yellow solid (0.887 g), mass spectrum (API+) 381 [MH+], C19H25FN2O5 requires 380.

Workup

  1. customThe reaction solution was then partitioned between ethyl acetate and water
  2. washthe organic solution was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was chromatographed over silica gel
  6. washeluting with 25 to 100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-32b31802fe894d738949ae6215f1fd8e
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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