HCID 68106205, compound → HCID 52914146, compound

HRID 531162Notes

Reaction equation

HRID 531162 reaction equation
C([O:8][C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][N:22]2[CH2:26][CH:27]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=3)[CH2:28][N:15]([CH2:16][CH2:17][CH2:18][N:19]([CH2:39][C:40]([O:42]CC3C=CC=CC=3)=[O:41])[CH2:20][CH2:21]2)[CH2:14][CH2:13]1)=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][N:22]2[CH2:26][CH:27]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([NH2:36])=[CH:34][CH:35]=3)[CH2:28][N:15]([CH2:16][CH2:17][CH2:18][N:19]([CH2:39][C:40]([OH:42])=[O:41])[CH2:20][CH2:21]2)[CH2:14][CH2:13]1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 68106205HCID 68106205, compound

Product 1

HCID 52914146HCID 52914146, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (1.19 g) was added to a solution of compound 30 (3.97 g, 5.91 mmol) in ethanol (100 mL). 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 28 (2.67 g, 98% 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-4f8b2d9db2ca46018b685c5b28b60f41
Source dataset
uspto-grants-2016_05
Patent number
US09353120B2

Reaction notes

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