Nitrogen → HCID 86736766, compound

HRID 1701268Notes

Reaction equation

HRID 1701268 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=[S:8].C(O[CH:14]1[NH:17][C:16](=[O:18])[CH2:15]1)(=O)C.N#N>[OH-].[K+].O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([O:9][CH:14]1[NH:17][C:16](=[O:18])[CH2:15]1)=[S:8]

Participants

6

Reactant 3

HCID 947NitrogenHCID 1199814-Acetoxy-2-azetidinoneHCID 178496264HCID 178496264, compound

Product 1

HCID 86736766HCID 86736766, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

To a solution of 2-methoxyethoxythioacetic acid (990 mg.; 6.60 mmoles) in 1 N KOH (6.0 ml.) and water (30 ml.) was added in an ice-bath under nitrogen atmosphere 4-acetoxy-2-azetidinone (777 mg.; 6.00 mmoles). The reaction mixture was stirred at room temperature (N2) for 1 hr. and then extracted with methylene chloride (30 ml.×3). The extracts were washed with brine, dried (Na2SO4) and evaporated yielding 4-(2-methoxyethoxythioacetoxy)-2-azetidinone (1.26 g.; 5.76 mmoles; 96% yield) as a yellow oil. nmr (CDCl3): δppm 2.8-3.8 (2H, m, H-3), 3.40 (3H, s, --OCH3), 3.4-3.9 (4H, m, --CH2CH2 --O), 4.25 (2H, s, O=CCH2O--), 5.25 (1H, dd, J3-4 cis =5 Hz, J3-4 trans =3 Hz, H-4), 7.3 (1H, br.s, --NH), ir (neat): 3280 cm-1 (γN--H), 1770 (γc=o, β-lactam), 1690 (γc=o, thioester).

Workup

  1. extractionand then extracted with methylene chloride (30 ml.×3)
  2. washThe extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-8c8c69f1a28b4ddb997bda1172db3f3a
Source dataset
uspto-grants-1980_03
Patent number
US04192801

Reaction notes

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