Triethylamine → 1-(1'-Carboxy-1'-chloromethyl)-4-tritylthio-2-azetidinone

HRID 893932Notes

Reaction equation

HRID 893932 reaction equation
C(N(CC)CC)C.[C:8]([CH:11]([N:13]1[CH:16]([S:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][C:14]1=[O:37])O)([OH:10])=[O:9].S(Cl)([Cl:40])=O>C(Cl)Cl>[C:8]([CH:11]([N:13]1[CH:16]([S:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][C:14]1=[O:37])[Cl:40])([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 127801621-(1'-Carboxy-1'-hydroxymethyl)-4-tritylthio-2-azetidinone

Product 1

HCID 139097231-(1'-Carboxy-1'-chloromethyl)-4-tritylthio-2-azetidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cooled (ice bath) solution of the triethylamine salt of 1-(1'-carboxy-1'-hydroxymethyl)-4-tritylthio-2-azetidinone (1.04 g, 2.0 mmol) in methylene chloride (5 ml) was treated dropwise, under N2, with thionyl chloride (0.16 ml, 2.2 mmol) in methylene chloride (2 ml). The solution was stirred at room temperature for 20 min and concentrated. The residue was diluted with benzene and filtered over a Celite/charcoal bed. The filtrate was evaporated in vacuo to give 870 mg (quantitative) of the title compound as an amorphous solid. It was used in the next step without further purification. ir νmax : 1775 cm-1 ; 1Hmr (CDCl3) δ: 9.22 (1H, bs), 7.27 (15H, m), 5.3 and 5.2 (1H, 2d, J=2 Hz), 4.6 (1H, m) and 2.8 ppm (2H, m).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with benzene
  3. filtrationfiltered over a Celite/charcoal bed
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-3f7d363a83764a9ba64699ce5d99eb9d
Source dataset
uspto-grants-1981_08
Patent number
US04282150

Reaction notes

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