HCID 68765971, compound → (1R,2S,5R)-tert-butyl 2-amino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate

HRID 2225297Notes

Reaction equation

HRID 2225297 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:14](=[O:15])[C@@H:13]2[CH2:16][C@H:9]1[CH2:10][CH2:11][C@@H:12]2[NH:17]C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:17][C@H:12]1[CH2:11][CH2:10][C@@H:9]2[CH2:16][C@H:13]1[C:14](=[O:15])[N:8]2[C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7]

Participants

4

Reactant 1

HCID 68765971HCID 68765971, compound

Product 1

HCID 68767611(1R,2S,5R)-tert-butyl 2-amino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Examples 11p and 11q, Step 1: To a solution of the (1R,2S,5R)-2-benzyloxycarbonylamino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylic acid tert-butyl ester (8 g, 21.36 mmoles) in 160 ml of methanol was added 1.6 g of 10% Pd/C (50% wet), and it was treated with H2 (52 psi)for 18 hrs. It was filtered through a plug of Celite to remove the catalyst, and the solvent was evaporated off to give (1R,2S,5R)-tert-butyl 2-amino-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate as a foamy solid, which was used for the next step without purification.

Workup

  1. additionwas treated with H2 (52 psi)for 18 hrs
  2. filtrationIt was filtered through a plug of Celite
  3. customto remove the catalyst
  4. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-d18fc24ef9aa430cab9ccf23880b76c8
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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