Triethylamine → 1-(1'-Carboxy-1'-hydroxymethyl)-4-tritylthio-2-azetidinone triethylamine salt

HRID 893931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 893931
[C:1]([S:20][CH:21]1[NH:24][C:23](=[O:25])[CH2:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH3:27].O.[C:34]([OH:38])(=[O:37])[CH:35]=[O:36]>O1CCCC1.C(Cl)Cl>[CH2:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH3:27].[C:34]([CH:35]([N:24]1[CH:21]([S:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:22][C:23]1=[O:25])[OH:36])([OH:38])=[O:37]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 127801644-Tritylthio-2-azetidinoneHCID 15620607Glyoxylic acid, monohydrate

Produkt 1

HCID 139097221-(1'-Carboxy-1'-hydroxymethyl)-4-tritylthio-2-azetidinone triethylamine saltAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-tritylthio-2-azetidinone (3.5 g, 10.15 mmol) in tetrahydrofuran (8 ml) was added triethylamine (1.42 ml, 10.15 mmol) and glyoxylic acid hydrate (1.02 g, 10.15 mmol). The mixture was stirred at room temperature with 4 A mol. sieves* (volume of 8 ml) for 1 h and allowed to stand at room temperature overnight. The solidified mixture was diluted with methylene chloride and filtered; the filtrate was evaporated and the residue crystallized from pentane to give 5.18 g (98%) of title compound as a white solid mp 112°-5° C.; ir νmax : 3100-3600, and 1755 cm-1 ; 1Hmr (CDCl3) δ:7.3 (15H, m), 4.92 and 5.10 (1H, 2s), 4.50 (1H, dd, J=8 Hz, J=3 Hz), 3.0 (1H, dd, J=15 Hz, J=7 Hz), 3.1 (6H, q, J=7 Hz), 2.70 (1H, dd, J=15 Hz, J=3 Hz), 2.0-3.5 (2H, m) and 1.21 ppm (9H, t, J=7 Hz).

Aufarbeitung

  1. waitto stand at room temperature overnight
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customthe residue crystallized from pentane

Quellen und Nachweise

ORD-Eintrag
ord-9da3c76d077243c8931d08822cfb8961
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04282150

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