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

HRID 893931Notes

Reaction equation

HRID 893931 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 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).

Workup

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

Sources & evidence

ORD record
ord-9da3c76d077243c8931d08822cfb8961
Source dataset
uspto-grants-1981_08
Patent number
US04282150

Reaction notes

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