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

HRID 30187

反応式

HRID 30187 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(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.

後処理

  1. customThe reaction solution was then partitioned between ethyl acetate and water the organic solution
  2. washwas 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

出典と根拠

ORDレコード
ord-6becd9c209224681b3840be6c555f791
出典データセット
uspto-grants-2008_09
特許番号
US07423052B2

関連ノート

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