Bromine → HCID 9957458, compound

HRID 1455883Notes

Reaction equation

HRID 1455883 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[C:10](=[C:28]([CH3:30])[CH3:29])[N:11]1[C:14](=[O:15])[C:13]([Br:17])([Br:16])[CH:12]1S(NCC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:32]Br>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:31])[C:10](=[C:28]([CH3:30])[CH3:29])[N:11]1[C:14](=[O:15])[C:13]([Br:17])([Br:16])[CH:12]1[Br:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 19372655HCID 19372655, compound

Product 1

HCID 9957458HCID 9957458, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,3-dibromo-alpha-(1-methylethylidene)-2-[benzylaminosulfinyl]-4-oxo-1-azetidine acetic acid benzyl ester (5.7 g; 0.01 mole) was dissolved in chloroform (120 mL), bromine on a polymer carrier (18.75 g; the content of bromine bound to the polymer matrix with polyvinylpyrrolidone was 26%, 0.03 mole) was added and it was stirred at room temperature for 48 hours. Then the polymer was sucked off and the filtrate was evaporated to dryness. The evaporated residue was passed through a silica gel column with methylene chloride to isolate 2,3,3-tribromo-alpha-(1-methylethylidene)-4-oxo-1-azetidine acetic acid benzyl ester (2.73 g; 55.0%), 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. additionwas added
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f14a9f9830774222983671cf14fe416b
Source dataset
uspto-grants-1998_12
Patent number
US05843939

Reaction notes

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