Pyridine → Benzyl 6-(alpha-azido-phenylacetamido)-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1154925Notes

Reaction equation

HRID 1154925 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]2[CH:3]1[CH2:4][C:5]([Cl:20])=[C:6]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].N1C=CC=CC=1.[N:27]([CH:30]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:31](Cl)=[O:32])=[N+:28]=[N-:29]>C(Cl)Cl>[N:27]([CH:30]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:31]([NH:1][CH:2]1[C:8](=[O:9])[N:7]2[CH:3]1[CH2:4][C:5]([Cl:20])=[C:6]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:32])=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 854292-Azido-2-phenylacetyl chlorideHCID 20563651Benzyl 6-amino-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 20563678Benzyl 6-(alpha-azido-phenylacetamido)-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of benzyl 6-amino-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (0.2 mmol) in methylene chloride (2 ml) containing anhydrous pyridine (0.1 ml) is added α-azidophenylacetyl chloride (0.2 mmol). After stirring in the cold for 60 mins, the solution is washed with water, pH 3 phosphate buffer, 5% sodium bicarbonate solution and brine, dried with magnesium sulfate, filtered, and evaporated under vacuum to give benzyl 6-(α-azido-phenylacetamido)-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washthe solution is washed with water, pH 3 phosphate buffer, 5% sodium bicarbonate solution and brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-65807b12b5c44cd98a94a02b7126a0cd
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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