HCID 68514786, compound → HCID 68516674, compound

HRID 1260406Notes

Reaction equation

HRID 1260406 reaction equation
C([O:8][C:9](=[O:30])[CH2:10][C@H:11]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:12][N:13]1[C:18](=[O:19])[CH2:17][CH2:16][CH:15]([CH3:20])[C:14]1=[O:21])C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:26]([O:25][C:23]([NH:22][C@H:11]([CH2:12][N:13]1[C:18](=[O:19])[CH2:17][CH2:16][CH:15]([CH3:20])[C:14]1=[O:21])[CH2:10][C:9]([OH:30])=[O:8])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 68514786HCID 68514786, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 68516674HCID 68516674, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-3-t-butoxycarbonylamino-4-(3-methyl-2,6-dioxo-piperidin-1-yl)-butyric acid benzyl ester (218 mg, 0.52 mmol) synthesized in Section (1) was dissolved in methanol and 10% Pd/C (22 mg, 0.1 eq) was added thereto, followed by stirring for 1 hour under 1 atm hydrogen gas. After the reaction was complete, Pd on charcoal was removed by celite filtration. The residue was purified by prep-TLC to afford 59 mg (yield: 35%) of the title compound.

Workup

  1. customPd on charcoal was removed by celite filtration
  2. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-afd368dea9c348aaa8ce2156adfa5979
Source dataset
uspto-grants-2013_06
Patent number
US08470836B2

Reaction notes

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