HCID 11404179, compound → HCID 67640568, compound

HRID 399521Notes

Reaction equation

HRID 399521 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@@H:7]1[CH2:11][C@H:10]([N:12]=[N+]=[N-])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:22])[C@@H:7]1[CH2:11][C@H:10]([NH2:12])[CH2:9][N:8]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 11404179HCID 11404179, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67640568HCID 67640568, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution (4S)-1-(tert-butyloxycarbonyl)-4-azido-L-proline tert-butyl ester (185 mg, 0.611 mmol) in 90% ethanol (15 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (40 mg) under a balloon atmosphere of hydrogen gas for one hour. The catalyst was removed by filtration through Celite, the filter washed with methanol, and the combined filtrate and washings evaporated. The title compound was obtained as a colorless oil after drying under high vacuum; yield 145 mg (86%).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washthe filter washed with methanol
  3. customthe combined filtrate and washings evaporated

Sources & evidence

ORD record
ord-a0f1cc08a5e7483d8fd8d258e1305653
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

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