HCID 86599410, compound → HCID 69215776, compound

HRID 1392177Notes

Reaction equation

HRID 1392177 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C@:7]23[CH2:14][C@H:13]([N:15]=[N+]=[N-])[CH2:12][N:11]2[C:10](=[O:18])[N:9]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)[C:8]3=[O:27])=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@:7]23[CH2:14][C@H:13]([NH2:15])[CH2:12][N:11]2[C:10](=[O:18])[N:9]([C:19]2[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=2)[C:8]3=[O:27])=[CH:28][CH:29]=1

Participants

4

Reactant 1

HCID 86599410HCID 86599410, compound

Product 1

HCID 69215776HCID 69215776, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (5R,7S)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-7-azido-1,3-diazabicyclo[3.3.0]octane-2,4-dione (0.83 g) in acetic acid (20 mL) was added zinc powder (0.90 g). After 1 hour at room temperature, the mixture was concentrated. The residue was suspended in satd. NaHCO3 and EtOAc. The mixture was filtered and the organic layer was collected, washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel: CH2Cl2: Chromatotron) afforded the titled compound (0.42 g). MS (m/z) 468 (MH+). mp 64.4° C.

Workup

  1. concentrationthe mixture was concentrated
  2. filtrationThe mixture was filtered
  3. customthe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by chromatography (silica gel: CH2Cl2: Chromatotron)

Sources & evidence

ORD record
ord-8189f4d5762548d4916aa6de3f6205f3
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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