Water → tert-Butyl {2-[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate

HRID 711008Notes

Reaction equation

HRID 711008 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][O:10][NH:11][C:12]([C@@H:14]1[CH2:20][CH2:19][C@@H:18]2[CH2:21][N:15]1[C:16](=[O:30])[N:17]2[O:22]CC1C=CC=CC=1)=[O:13])([CH3:4])([CH3:3])[CH3:2].O>O1CCCC1.[Pd]>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][O:10][NH:11][C:12]([C@@H:14]1[CH2:20][CH2:19][C@@H:18]2[CH2:21][N:15]1[C:16](=[O:30])[N:17]2[OH:22])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 962WaterHCID 72549867tert-Butyl {2-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate

Product 1

HCID 86699591tert-Butyl {2-[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamateYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl{2-[({[(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]ethyl}carbamate (43.4 g, 100 mmol) was dissolved in tetrahydrofuran (475 mL). After the dissolution was confirmed, water (25 mL) was added, and set under an argon atmosphere. 10% Pd/C (8.68 g, 50% wet) was added, and stirred vigorously under hydrogen atmosphere for 3 h. The end point was confirmed by TLC, and then catalyst was filtered through Celite. The solvent of filtrate was concentrated under reduced pressure. The concentrated residue was subjected to workup of substitution and concentration with ethyl acetate (100 mL) twice, and with methylene chloride (100 mL) once to afford 34.5 g of the title compound (quantitative). Instrumental data were consistent with those of Example 59.

Workup

  1. dissolutionAfter the dissolution
  2. filtrationcatalyst was filtered through Celite
  3. concentrationThe solvent of filtrate was concentrated under reduced pressure
  4. concentrationThe concentrated residue was subjected to workup of substitution and concentration with ethyl acetate (100 mL) twice

Sources & evidence

ORD record
ord-4a2df2d241ee4ca3bda5615756cff533
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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