1-Hydroxybenzotriazole → N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-3-hydroxy-2,2-dimethylpropanamide

HRID 1987302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987302
Cl.[NH2:2][CH:3]([CH:5]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:4].[OH:21][CH2:22][C:23]([CH3:28])([CH3:27])[C:24](O)=[O:25].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[CH:3]([NH:2][C:22](=[O:21])[C:23]([CH3:28])([CH3:27])[CH2:24][OH:25])[CH3:4])=[CH:19][CH:18]=1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 785483-Hydroxy-2,2-dimethylpropionic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222704272,3-Bis(4-chlorophenyl)-1-methylpropylamine hydrochloride

Produkt 1

HCID 22270540N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-3-hydroxy-2,2-dimethylpropanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-3,4-bis(4-chlorophenyl)butane hydrochloride salt (Reference Example 1, Diastereomer a) (3.7 g, 11 mmol), 3-hydroxy-2,2-dimethylpropionic acid (2.0 g, 17 mmol) in CH2Cl2 (100 mL) was added 1-hydroxybenzotriazole (2.3 g, 17 mmol), diisopropylethylamine (7.7 mL, 44 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.2 g, 17 mmol). After stirring at room temperature overnight. The reaction mixture was diluted with EtOAc (200 mL), washed with water and saturated aqueous sodium bicarbonate, and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluted with 50% EtOAc in hexane to give the title compound. 1H NMR (500 MHz, CD3OD): δ7.24 (d, 2H), 7.12 (d, 2H), 7.10 (d, 2H), 6.92 (d, 2H), 4.25 (m, 1H), 3.68 (ABq, 2H), 3.18 (dd, 1H), 2.93 (ddd, 1H), 2.76 (dd, 1H), 1.20 (s, 3H), 1.19 (s, 3H), 0.96 (d, 3H). LC-MS: m/e 394 (M+H)+ (3.5 min).

Aufarbeitung

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. concentrationconcentrated to dryness
  3. customthe residue was purified by flash column chromatography on silica gel
  4. washeluted with 50% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-470187f6825c41cabe2b8a2e5c1eee4a
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550489B2

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