t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate → t-Butyl alpha-[3(S*)-amino-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate

HRID 569757Notes

Reaction equation

HRID 569757 reaction equation
[N:1]([C@@H:4]1[CH2:10][CH2:9][C@@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][N:6]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:5]1=[O:25])=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][C@@H:4]1[CH2:10][CH2:9][C@@H:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][N:6]([CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:5]1=[O:25]

Participants

5

Reactant 2

HCID 14003443t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 14003450t-Butyl alpha-[3(S*)-amino-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.3 g of 5% w/w palladium-on-carbon was added to 30 ml of ethanol containing 1.4 g of t-butyl α-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate (Isomer A) [prepared as described in Example 1(h)], and under one atmosphere pressure of hydrogen the reaction mixture was shaken for 4 hours at 40° C. The catalyst was filtered off and the solvent was evaporated under reduced pressure, to give 1.56 g of the title compound as a gummy substance.

Workup

  1. custom[prepared as described in Example 1(h)]
  2. filtrationThe catalyst was filtered off
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-937c9b542ff5470289cf2296ca2abbce
Source dataset
uspto-grants-1988_03
Patent number
US04734410

Reaction notes

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