Water → trans-7-Chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester

HRID 1771

Reaktionsgleichung

Reaktionsgleichung von HRID 1771
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:10](=[O:16])[C@@H:9]([CH2:17][C:18]([OH:20])=[O:19])[O:8][C@H:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:6]=2[CH:28]=1.[C:29]([O:35][CH2:36]Cl)(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C(N(CC)CC(C)C)C(C)C.O>CN(C)C=O.C(OCC)(=O)C>[C:29]([O:35][CH2:36][O:19][C:18](=[O:20])[CH2:17][C@H:9]1[O:8][C@H:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[C:6]2[CH:28]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[C:10]1=[O:16])(=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31]

Komponenten

7

Edukt 4

HCID 962WaterHCID 87885Chloromethyl pivalateHCID 12446309N-Ethyl-2-methyl-N-(2-methylpropyl)propan-1-amineHCID 22883210trans-7-Chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

Produkt 1

HCID 67603055trans-7-Chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In N,N-dimethylformamide (10 ml) was dissolved trans- 7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (0.5 g) obtained in Example 2. To the solution were added pivaloyloxymethyl chloride (0.43 ml), N,N-diisobutyl ethylamine (0.52 ml) and KI (0.2 g). The mixture was stirred at room temperature overnight. To the reaction mixture were added water (100 ml) and ethyl acetate (100 ml), followed by extraction. The ethyl acetate layer was washed with an aqueous solution of potassium hydrogensulfate, an aqueous solution of sodium hydrogencarbonate and water, successively, which was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to afford trans-7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester (0.55 g).

Aufarbeitung

  1. extractionfollowed by extraction
  2. washThe ethyl acetate layer was washed with an aqueous solution of potassium hydrogensulfate
  3. dry with materialan aqueous solution of sodium hydrogencarbonate and water, successively, which was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-157fb9c3937847cf98e7bf4bb5a1bfb6
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726306

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