6-[acetoxy-(5-methoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester → 6-(5-methoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-ylmethylene)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1744971Notes

Reaction equation

HRID 1744971 reaction equation
[N+](C1C=CC(C[O:9][C:10]([C:12]2[N:13]3[CH:16]([S:17][CH:18]=2)[C:15]([CH:20](OC(=O)C)[C:21]2[N:32]=[C:31]4[N:23]([C:24]5[CH2:25][CH2:26][CH2:27][C:28]=5[C:29]([O:33][CH3:34])=[N:30]4)[CH:22]=2)(Br)[C:14]3=[O:39])=[O:11])=CC=1)([O-])=O.[H][H]>C1COCC1.P([O-])([O-])([O-])=O>[CH3:34][O:33][C:29]1[C:28]2[CH2:27][CH2:26][CH2:25][C:24]=2[N:23]2[C:31](=[N:32][C:21]([CH:20]=[C:15]3[C:14](=[O:39])[N:13]4[CH:16]3[S:17][CH:18]=[C:12]4[C:10]([OH:11])=[O:9])=[CH:22]2)[N:30]=1

Participants

5

Reactant 2

HCID 687056406-[acetoxy-(5-methoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 687033696-(5-methoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-ylmethylene)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-[acetoxy-(5-methoxy-7,8-dihydro-6H-3,4,8b-triaza-as-indacen-2-yl)-methyl]-6-bromo-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (966 mg, 1.4 mmol) was suspended in 20 ml THF and 20 ml pH=6.5 aqueous phosphate buffer. The mixture was then subjected to 45 psi hydrogen for two hours. Then it was filtered through a pad of celite and concentrated in vacuo to remove most of the THF. The solution was then cooled to zero degree and basified to pH=8 with 1 N sodium hydroxide. Then it was purified via reverse phase HPLC using 1 liter of water followed by 5%-25% acetonitrile and water. Water was then removed through concentrate in vacuo and 100 mg of product was collected.

Workup

  1. filtrationThen it was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customto remove most of the THF
  4. temperatureThe solution was then cooled to zero degree and basified to pH=8 with 1 N sodium hydroxide
  5. customThen it was purified via reverse phase
  6. customWater was then removed
  7. concentrationthrough concentrate in vacuo and 100 mg of product
  8. customwas collected

Sources & evidence

ORD record
ord-93b276ddf96848b5943a6fde2f9d0661
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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