HCID 86744216, compound → HCID 86744215, compound

HRID 1032365Notes

Reaction equation

HRID 1032365 reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][O:13][P:14]([CH2:19][N:20]1[C@H:23]([CH2:24][CH2:25][CH:26]2[O:31]CCO[CH2:27]2)[C@H:22]([N:32]=[N+:33]=[N-:34])[C:21]1=[O:35])([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>S(=O)(=O)(O)O.C(O)(=O)C>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][O:13][P:14]([CH2:19][N:20]1[C@H:23]([CH2:24][CH2:25][C:26](=[O:31])[CH3:27])[C@H:22]([N:32]=[N+:33]=[N-:34])[C:21]1=[O:35])([O:16][CH2:17][CH3:18])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86744216HCID 86744216, compound

Product 1

HCID 86744215HCID 86744215, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

A suspension of cis-1-(benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-(3-ethylenedioxybutyl)-2-azetidinone (0.10 g.) in 10% aqueous sulfuric acid (8 ml.) and glacial acetic acid (1 ml.) is heated with stirring at 50° for 2 hrs. The mixture is cooled to room temperature and extracted with methylene chloride (3×15 ml.) The combined extracts are washed with brine (2×10 ml.), dried with magnesium sulfate, filtered, and evaporated in vacuo to yield 60% of cis-1-(benzyloxycarbonyldiethylphosphono)methyl-3-azido-4-(3-oxobutyl)-2-azetidinone as a light brown oil. NMR (CDCl3) δ: 1.27 (m, O--CH2 --CH3); 2.13 (s, CH3); 4.12 (m, O--CH2CH3 and H4); 4.72 (d, J=5.5 Hz, H3); 5.23 (s, OCH2 φ); 7.35 (φ). IR (film) μ: 4.70 (N3); 5.61 (β-lactam); 5.70 (ester); 5.82 (C= O) M+ (Calc. 466) Found 466.

Workup

  1. temperatureis heated
  2. extractionextracted with methylene chloride (3×15 ml.) The combined extracts
  3. washare washed with brine (2×10 ml.)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5ebb9f32057c40faafeec2744f923c5f
Source dataset
uspto-grants-1990_09
Patent number
US04957912

Reaction notes

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