HCID 131723769, compound → HCID 11447897, compound

HRID 1059087Notes

Reaction equation

HRID 1059087 reaction equation
Cl.[CH:2]1([C@@H:8]([NH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:9]([O:11]CC2C=CC=CC=2)=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C(O)(C)C.[Pd]>[CH:2]1([C@@H:8]([NH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:9]([OH:11])=[O:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 131723769HCID 131723769, compound

Product 1

HCID 11447897HCID 11447897, compoundYield 201.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Benzyl (2R)-2-cyclohexyl-2-[(2-ethoxy-2-oxoethyl)amino]ethanoate hydrochloride (40 g, 0.1 mol, from step (b) above) dissolved in iso-propyl alcohol (320 mL) was hydrogenated in the presence of 5% Pd/C (2 g, 50% aq.) for 3 h at 30° C. After removal of the catalyst by filtration, the filtrate was neutralised with tetrabutylammonium hydroxide and the pH was adjusted to 5.2. To rid the resultant of water, the suspension was evaporated and washed repeatedly with iso-propylalcohol and dried to yield 49 g (94%) of the sub-title compound.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe suspension was evaporated
  4. washwashed repeatedly with iso-propylalcohol
  5. customdried

Sources & evidence

ORD record
ord-d34c01a60afd4f9eb3d240f8fa378b50
Source dataset
uspto-grants-2003_02
Patent number
US06518434B2

Reaction notes

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