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

HRID 1680360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1680360
[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 4A 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=3Hz), 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=3Hz), 2.0-3.5 (2H, m) and 1.21 ppm (9H, t, J=7 Hz).

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate was evaporated
  3. customthe residue crystallized from pentane

Quellen und Nachweise

ORD-Eintrag
ord-95fa268d25a34af880358dd4a9564ba5
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04272437

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