Diethyl Ether → HCID 89303250, compound

HRID 1523116Notes

Reaction equation

HRID 1523116 reaction equation
[C:1]([CH2:8][N:9]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][N:15]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:13][N:12]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-])=O)=[CH:33][CH:32]=2)[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCOCC>C(O)C.[Pd]>[C:1]([CH2:8][N:9]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16][N:15]([CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:14][CH2:13][N:12]([CH2:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]([NH2:37])=[CH:35][CH:36]=2)[CH2:11][CH2:10]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 71133753HCID 71133753, compound

Product 1

HCID 89303250HCID 89303250, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound (25) (1.35 g, 2.46 mmol) in absolute ethanol (100 ml) was added 10% Pd/C (0.41 g). The resultant mixture was stirred at an ambient temperature in the presence of H2 (g) for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 ml). The filtrate was evaporated in vacuo to give an oily residue, which was then treated with Et2O to obtain a white solid of compound (26) (1.25 g, 98% yield).

Workup

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

Sources & evidence

ORD record
ord-eb77aecc8ed54b1eb7a3b1a41ed6d8d5
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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