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Methyl iodide → (S)-2-Methoxycarbonylmethyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

HRID 1963068
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HRID 1963068 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@@H:13]([CH2:24][C:25]([OH:27])=[O:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][C@@H:13]1[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:18])([CH3:22])([CH3:23])[CH3:21]
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참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68205818[(S)-4-Benzyloxycarbonyl-1-tert-butoxycarbonyl-piperazin-2-yl]-acetic acid

생성물 1

HCID 67772911(S)-2-Methoxycarbonylmethyl-piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester수율 89.3%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of the compound of step 1 (2.52 g, 6.66 mmol) in 45 ml of acetone were added potassium carbonate (5.522 g, 39.96 mmol) and iodomethane (1.24 ml, 19.98 mmol) and the solution was stirred at room temperature overnight. The mixture was filtered and the filtrate was concentrated to dryness. The residue was dissolved in EA, washed twice with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 85:15) to give 2.334 g of the title compound as a colorless oil.

후처리

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe residue was dissolved in EA
  4. washwashed twice with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

출처 및 근거

ORD 기록
ord-449a547b11ce4819919a2983f7b03f26
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415336B2

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