Benzyl 6-azido-3-chloro-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate → Benzyl 6-amino-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1154924Notes

Reaction equation

HRID 1154924 reaction equation
[N:1]([CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([Cl:22])=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[N+]=[N-]>[Pt]=O.C(OCC)(=O)C>[NH2:1][CH:4]1[C:10](=[O:11])[N:9]2[CH:5]1[CH2:6][C:7]([Cl:22])=[C:8]2[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

4

Reactant 1

HCID 20563652Benzyl 6-azido-3-chloro-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylate

Product 1

HCID 20563651Benzyl 6-amino-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of platinum oxide (100 mg), benzyl 6-azido-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (80 mg), and ethyl acetate (2 ml) is hydrogenated on a Paar shaker for 30 mins at 45 psi. The resulting mixture is filtered through a pad of silica gel G which is washed with additional ethyl acetate. The filtrate is washed with water and brine, dried with magnesium sulfate, and evaporated under vacuum to afford benzyl 6-amino-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. filtrationThe resulting mixture is filtered through a pad of silica gel G which
  2. washis washed with additional ethyl acetate
  3. washThe filtrate is washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-c0d303d3792e40a7b7895796a3a8632b
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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