HCID 130217018, compound → HCID 89832823, compound

HRID 1424518Notes

Reaction equation

HRID 1424518 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]1[CH:22]=[C:21]([CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[O:20][N:19]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[C:27]([O:26][C:25](=[O:31])[NH:24][CH2:23][C:21]1[O:20][N:19]=[C:18]([C@@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[OH:8])[CH:22]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 1

HCID 130217018HCID 130217018, compound

Product 1

HCID 89832823HCID 89832823, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)isoxazol-5-yl)methylcarbamate (210 mg, 0.5 mmol) in THF (5 mL) was added 10% Pd/C (100 mg). The reaction mixture was then filtered and concentrated to afford tert-butyl((3-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)isoxazol-5-yl)methyl)carbamate (180 mg, 99%) as a light yellow solid, which was used directly in the next step. ESI-MS (EI+, m/z): 339.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6bb197b2ef4e4d3fbb33a0243567319c
Source dataset
uspto-grants-2015_01
Patent number
US08927724B2

Reaction notes

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