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

HRID 1680360Notes

Reaction equation

HRID 1680360 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-95fa268d25a34af880358dd4a9564ba5
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

Loading…