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Potassium Carbonate → 4'-Acetamido-2'-benzyloxy-2-[4-(benzyloxycarbonyl)piperazin-1-yl]acetophenone

HRID 1433156
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433156
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([NH:35][C:36](=[O:38])[CH3:37])[CH:28]=[CH:29][C:30]=1[C:31](=[O:34])[CH2:32]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:36]([NH:35][C:27]1[CH:28]=[CH:29][C:30]([C:31](=[O:34])[CH2:32][N:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:12][CH2:13]2)=[C:25]([O:24][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:26]=1)(=[O:38])[CH3:37]
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 85606679N-[3-benzyloxy-4-(2-bromo-acetyl)phenyl]-acetamide

Produkt 1

HCID 690575444'-Acetamido-2'-benzyloxy-2-[4-(benzyloxycarbonyl)piperazin-1-yl]acetophenoneAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

1-(Benzyloxycarbonyl)piperazine (117 μL, 134 mg, 0.607 mmol) was added to a mixture of N-[3-benzyloxy-4-(2-bromo-acetyl)phenyl]-acetamide (200 mg, 0.552 mmol) and potassium carbonate (115 mg, 0.828 mmol) in DMF (5 mL), and stirred at room temperature for 18 hours. The solvent was removed in vacuo, and taken up in brine (25 mL). The aqueous was extracted with DCM (3×25 mL) and the combined organics dried (MgSO4). The solvents were removed in vacuo, and the product was purified by preparative HPLC to give pure 4′-acetamido-2′-benzyloxy-2-[4-(benzyloxycarbonyl)piperazin-1-yl]acetophenone (114 mg, 41%, 50% rec.) as an off-white solid; δH (CDCl3) 8.23 (1H, br s), 7.81 (1H, d, J=8.6 Hz), 7.77-7.76 (1H, m), 7.53-7.51 (2H, m), 7.42-7.28 (8H, m), 7.08 (1H, dd, J=8.6, 1.8 Hz), 5.20 (2H, s), 5.12 (2H, s), 4.00 (2H, s), 3.59-3.48 (4H, m), 2.65-2.60 (4H, m), 2.14 (3H, s); LCMS retention time 2.07 min, M+H+ 502.5, along with recovered N-(4-acetyl-3-benzyloxy-phenyl)-acetamide (35 mg).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. extractionThe aqueous was extracted with DCM (3×25 mL)
  3. dry with materialthe combined organics dried (MgSO4)
  4. customThe solvents were removed in vacuo
  5. customthe product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-563f8ad0daf74a0eb68aadd7d6a69792
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612201B2

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