HCID 90088573, compound → HCID 90088586, compound

HRID 517673Notes

Reaction equation

HRID 517673 reaction equation
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]#[N:19])C1C=CC=CC=1>C(OCC)(=O)C.O1CCCC1.[Pd]>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]#[N:19]

Participants

5

Reactant 1

HCID 90088573HCID 90088573, compound

Product 1

HCID 90088586HCID 90088586, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonitrile (XIII) (1 gm, 0.00389 mol) in a mixture of ethyl acetate and tetrahydrofuran (THF) (4:6, 4 ml:6 ml) containing 10% palladium over carbon (0.300 gm, 50% wet) was hydrogenated at 50-55 psi, for 6 hours at 25° C. The resulting mixture was filtered through a celite pad and residue was washed with mixture of ethyl acetate and tetrahydrofuran (4:6, 4 ml:6 ml). The solvent from the combined filtrate was evaporated under reduced pressure to obtain 0.649 gm of the titled compound of Formula (XIIIa) as oil, which was used as such for the next reaction without further purification.

Workup

  1. filtrationThe resulting mixture was filtered through a celite pad and residue
  2. washwas washed with mixture of ethyl acetate and tetrahydrofuran (4:6, 4 ml:6 ml)
  3. customThe solvent from the combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e5aeb6c6664b4f51a08699c77283f0f4
Source dataset
uspto-grants-2015_08
Patent number
US09115131B2

Reaction notes

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