N-bromobutanimide → HCID 9957458, compound

HRID 1455882Notes

Reaction equation

HRID 1455882 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[C:10](=[C:27]([CH3:29])[CH3:28])[N:11]1[C:14](=[O:15])[C:13]([Br:17])([Br:16])[CH:12]1S(C1C=C(C)ON=1)(N)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:30])[C:10](=[C:27]([CH3:29])[CH3:28])[N:11]1[C:14](=[O:15])[C:13]([Br:17])([Br:16])[CH:12]1[Br:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178447472HCID 178447472, compound

Product 1

HCID 9957458HCID 9957458, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,3-dibromo-alpha-(1-methylethylidene)-2-[(5-methyl-isoxazole-3-yl)-aminosulfinyl]-4-oxo-1-azetidine acetic acid benzyl ester (5.61 g; 0.01 mole) was dissolved in chloroform (120 mL), N-bromosuccinimide (7.12 g; 0.04 mole) was added to the reaction mixture and it was stirred for two hours at room temperature. The reaction mixture was evaporated, methylene chloride and n-hexane were added to the dry residue, the precipitate was sucked off and the filtrate was evaporated to a dry residue. The obtained product was purified by flash chromatography with the solvent system petroleum ether-methylene chloride (1:1). There was obtained 2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester (3.05 g, 61.5%), which was subjected to a reaction with silver tetrafluoroborate in methanol analogously to the reaction described under 1a. After isolation 3,3-dibromo-2-methoxy-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester with spectroscopic data identical to those disclosed under 1a was obtained.

Workup

  1. customThe reaction mixture was evaporated
  2. additionmethylene chloride and n-hexane were added to the dry residue
  3. customthe filtrate was evaporated to a dry residue
  4. customThe obtained product was purified by flash chromatography with the solvent system petroleum ether-methylene chloride (1:1)

Sources & evidence

ORD record
ord-328aba15277d4c38bba523dbe433f6f2
Source dataset
uspto-grants-1998_12
Patent number
US05843939

Reaction notes

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