Diisopropylethylamine → Rac-4-(2-iodo-5-methanesulfonyl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 32737

Reaktionsgleichung

Reaktionsgleichung von HRID 32737
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:15][C:16]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:17]=1[C:18](O)=[O:19].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:18](=[O:19])[C:17]2[CH:21]=[C:22]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:23]=[CH:24][C:16]=2[I:15])[CH:10]([CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylateHCID 574452812-Iodo-5-methanesulfonyl-benzoic acid

Produkt 1

HCID 59793735Rac-4-(2-iodo-5-methanesulfonyl-benzoyl)-3-methyl-piperazine-1-carboxylic acid tert-butyl esterAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of rac-3-Methyl-piperazine-1-carboxylic acid tert-butyl ester (350 mg, 1.75 mmol) in dimethylformamide (3 ml) were added 2-Iodo-5-methanesulfonyl-benzoic acid (540 mg, 1.67 mmol), N-ethyldiisopropylamine (1.8 ml, 10.5 mmol), and TBTU (630 mg, 1.92 mmol). The reaction mixture was then allowed to stir at room temperature for 16 hours. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2, 20 g, Heptane/EtOAc 0-100%) to give the title compound (400 mg, 45%). MS (m/e): 526.2 (M+NH4+).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified by column chromatography (SiO2, 20 g, Heptane/EtOAc 0-100%)

Quellen und Nachweise

ORD-Eintrag
ord-edf9f4fdab1941119255d8969f0c13db
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427612B2

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