HCID 52914148, compound → HCID 52914147, compound

HRID 531161Notes

Reaction equation

HRID 531161 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][N:19]2[CH2:23][CH:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=3)[CH2:25][N:12]([CH2:13][CH2:14][CH2:15][N:16]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:17][CH2:18]2)[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)C.[Pd]>[C:37]([CH2:36][N:16]1[CH2:15][CH2:14][CH2:13][N:12]2[CH2:25][CH:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=3)[CH2:23][N:19]([CH2:20][CH2:21][CH2:22][N:9]([CH2:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:10][CH2:11]2)[CH2:18][CH2:17]1)([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38]

Participants

4

Reactant 1

HCID 52914148HCID 52914148, compound

Product 1

HCID 52914147HCID 52914147, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound 26 (4.26 g, 7.06 mmol) in ethanol (100 mL) was added 10% Pd/C (1.28 g). The resulting mixture was stirred under H2 (g) atmosphere at room temperature for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 mL). The combined filtrate was evaporated in vacuo to give an oily residue which was triturated with Et2O to provide an off-white solid 27 (3.93 g, 97% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashed with ethanol (2×20 mL)
  3. customThe combined filtrate was evaporated in vacuo
  4. customto give an oily residue which
  5. customwas triturated with Et2O

Sources & evidence

ORD record
ord-48e4316dc3eb4d66bfefb76fa60559d6
Source dataset
uspto-grants-2016_05
Patent number
US09353120B2

Reaction notes

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