Diisopropylcarbodiimide → 4-[4-[[(Phenylmethoxy)amino]carbonyl]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester

HRID 538083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538083
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)(O)=[O:2].Cl.[C:24]1([CH2:30][O:31][NH2:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:24]1([CH2:30][O:31][NH:32][C:1]([C:4]2[CH:5]=[CH:6][C:7]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[CH:8][CH:9]=2)=[O:2])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 3

HCID 12734DiisopropylcarbodiimideHCID 102312Benzyloxyamine hydrochlorideHCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Produkt 1

HCID 865982014-[4-[[(Phenylmethoxy)amino]carbonyl]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl esterAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-carboxyphenyl)-1-piperazinecarboxylic acid, 1-(1,1-dimethylethyl) ester (0.032 mol), O-(phenylmethyl)-hydroxylamine hydrochloride (0.064 mol), DMAP (0.03 mol) in DCM p.a. (250 ml) and TEA (14 ml) was stirred at room temperature. DIC (0.064 mol) was added. The reaction mixture was stirred at room temperature for 8 hours, then washed with water, HCl (0.5N) and water. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: DCM/MeOH 98/2). The desired fractions were collected and the solvent was evaporated, yielding 13.7 g of 4-[4-[[(phenylmethoxy)amino]carbonyl]phenyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (interm. 4).

Aufarbeitung

  1. washwashed with water, HCl (0.5N) and water
  2. dry with materialThe separated organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: DCM/MeOH 98/2)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-21f71e6f95f046308cd25ba1e72bc7f3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865720B2

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