Triethylamine → Methyl cis-1-(2,4-Dimethoxybenzyl)-3-phenoxyacetamido-4-oxo-2-azetidinecarboxylate

HRID 127892

Reaction equation

HRID 127892 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@H:8]([NH2:11])[C@@H:7]1[C:12]([O:14][CH3:15])=[O:13].C(N(CC)CC)C.[O:29]([CH2:36][C:37](Cl)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@H:8]([NH:11][C:37](=[O:38])[CH2:36][O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:7]1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 18632686Methyl cis-1-(2,4-Dimethoxybenzyl)-3-amino-4-oxoazetidine-2-carboxylate

Product 1

HCID 70577439Methyl cis-1-(2,4-Dimethoxybenzyl)-3-phenoxyacetamido-4-oxo-2-azetidinecarboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

The crude amine prepared in Example 2 from 10 g of the azido precursor is taken up in 100 ml of anhydrous methylene dichloride and is cooled to 0° in an ice bath. To this solution is added 4.32 ml (0.0312 mol) of triethylamine followed by the slow addition of a solution of 5.32 g (0.0312 mol) of phenoxyacetyl chloride in 40 ml of methylene dichloride. The mixture is stirred at 0° for 1 hr. then poured into a separatory funnel and extracted successively with water, aqueous HCl, aqueous NaHCO3, brine and is dried over anhydrous magnesium sulfate. After filtration the solvent is removed in vacuo to give a yellow solid. This material is partially dissolved in ether, cooled to -25°, and filtered to afford 11.2 g (84%) of the title product as a white solid which is one spot on tlc: benzene-ethyl acetate (1:1), silica gel, Rf 0.38. An analytical sample, mp 115.5°-116.0°, is obtained by recrystallization from ethyl acetate-hexane.

Workup

  1. temperatureis cooled to 0° in an ice bath
  2. additionthen poured into a separatory funnel
  3. extractionextracted successively with water, aqueous HCl, aqueous NaHCO3, brine
  4. dry with materialis dried over anhydrous magnesium sulfate
  5. filtrationAfter filtration the solvent
  6. customis removed in vacuo
  7. customto give a yellow solid
  8. temperaturecooled to -25°
  9. filtrationfiltered

Sources & evidence

ORD record
ord-f003fc53ffc94e068a6b49df21ae3ee1
Source dataset
uspto-grants-1981_03
Patent number
US04257947

Linked notes

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