Chlorotrimethylsilane → (3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 1979901Notes

Reaction equation

HRID 1979901 reaction equation
[CH2:1]([N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH3:18][C@@H:19]1[N:22]([S:23]([O-:26])(=[O:25])=[O:24])[C:21](=[O:27])[C@H:20]1[NH:28][C:29]([O:31]C1C=CC=CC=1)=O.[CH2:38](N(CC)CC)[CH3:39].[CH3:45][Si](C)(C)Cl>ClCCCl>[CH2:14]([N+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:15][CH2:16][CH3:17].[CH3:18][C@@H:19]1[N:22]([S:23]([O-:26])(=[O:25])=[O:24])[C:21](=[O:27])[C@H:20]1[NH:28][C:29](=[O:31])[CH2:45][C:17]1[CH:16]=[CH:15][CH:14]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 131713967(3S-trans)-4-methyl-2-oxo-3-(phenyloxycarbonylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 131713000(3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 531 mg (0.001 mole) of (3S-trans)-4-methyl-2-oxo-3-(phenyloxycarbonylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt, in 15 ml of 1,2-dichloroethane is refluxed for 90 minutes with 278 μl of triethylamine and 250 μl of trimethylchlorosilane. After distillation of 5 ml of solvent, a solution of 136 mg of phenylacetic acid and 140 μl of triethylamine in 1 ml of dimethylformamide is added and the mixture is refluxed for 2 hours. The reaction mixture is poured into water and extracted into dichloromethane. After washing with saturated sodium bicarbonate solution, the organic layer is dried and evaporated. Trituration with ether gives 239 mg of (3S-trans)-4-methyl-2-oxo-3-(phenylacetylamino)-1-azetidinesulfonic acid, tetrabutylammonium salt.

Workup

  1. distillationAfter distillation of 5 ml of solvent
  2. additiona solution of 136 mg of phenylacetic acid and 140 μl of triethylamine in 1 ml of dimethylformamide is added
  3. temperaturethe mixture is refluxed for 2 hours
  4. additionThe reaction mixture is poured into water
  5. extractionextracted into dichloromethane
  6. washAfter washing with saturated sodium bicarbonate solution
  7. customthe organic layer is dried
  8. customevaporated

Sources & evidence

ORD record
ord-5606b35912aa4c6a9d5e5ff6af37ad54
Source dataset
uspto-grants-1984_11
Patent number
US04483797

Reaction notes

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