Tetrahydrofuran → 3-Diphenylmethoxycarbonyl-1-(2-benzyloxycarbonylamino-4-thiazolyl)-2-propene-1,1-dicarboxylic acid diethyl ester

HRID 1906538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906538
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([C:11]1[N:12]=[C:13]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[S:14][CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].Cl/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].O1[CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)(=O)C.Cl>[CH2:9]([O:8][C:6]([C:5]([C:11]1[N:12]=[C:13]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[S:14][CH:15]=1)([C:4]([O:3][CH2:1][CH3:2])=[O:27])[CH:31]=[CH:32][C:33]([O:35][CH:37]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:38]1[CH:6]=[CH:5][CH:4]=[CH:40][CH:39]=1)=[O:34])=[O:7])[CH3:10]

Komponenten

7

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 638124trans-3-Chloroacrylic acidHCID 136714242-(2-Benzyloxycarbonylamino-4-thiazolyl)malonic acid diethyl ester

Produkt 1

HCID 541243823-Diphenylmethoxycarbonyl-1-(2-benzyloxycarbonylamino-4-thiazolyl)-2-propene-1,1-dicarboxylic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-benzyloxycarbonylamino-4-thiazolyl)malonic acid diethyl ester in tetrahydrofuran (20 parts) are added sodium hydride (2.35 equivalents) and a solution of trans-3-chloroacrylic acid diphemylmethyl ester (1.2 equivalents) in tetrahydrofuran (8 parts) under ice cooling. After stirring at 35° to 40° C. for 12.5 hours, the mixture is diluted with ethyl acetate and diluted hydrochloric acid, washed with water, dried, and concentrated. The residue is chromatographed over silica gel. The fraction eluted with a mixture of benzene and ethyl acetate (15:1) is crystallized from ethyl acetate to give 3-diphenylmethoxycarbonyl-1-(2-benzyloxycarbonylamino-4-thiazolyl)-2-propene-1,1-dicarboxylic acid diethyl ester.

Aufarbeitung

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue is chromatographed over silica gel
  5. washThe fraction eluted with a mixture of benzene and ethyl acetate (15:1)
  6. customis crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b2a4fb4ac36a474cb71c797adfe8b550
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04652652

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