Diethyl Ether → HCID 89303282, compound

HRID 1523114Notes

Reaction equation

HRID 1523114 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][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=2)[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCOCC>C(O)C.[Pd].C([O-])([O-])=O.[Ca+2]>[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]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:14][CH2:13][N:12]([CH2:29][C:30]2[CH:31]=[CH:32][C:33]([NH2:36])=[CH:34][CH:35]=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 71133773HCID 71133773, compound

Product 1

HCID 89303282HCID 89303282, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound (21) (1.72 g, 3.21 mmol) in absolute ethanol (100 ml) was added 5% Pd/CaCO3 (0.31 g) to which lead (Pb) had been added as an inhibitor. 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 (22) (1.59 g, 98% yield).

Workup

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

Sources & evidence

ORD record
ord-2713ffe7b51c474993b18b3d6b62bfdf
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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