Diethyl Ether → HCID 89303294, compound

HRID 1523106Notes

Reaction equation

HRID 1523106 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:15][CH2:14][CH2:13][N:12]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=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[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:15][CH2:14][CH2:13][N:12]([CH2:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([NH2:39])=[CH:37][CH:38]=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 71133877HCID 71133877, compound

Product 1

HCID 89303294HCID 89303294, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound (8) (1.15 g, 1.99 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 under H2 atmosphere for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 ml). The solvent was evaporated from the combined filtrate in vacuo to give an oily residue, which was then treated with Et2O to obtain a white solid of compound (10) (1.09 g, 98% yield). 1H NMR (500 MHz, CDCl3): δ 6.90-6.88 (dd, 2H), 6.55-6.54 (dd, 2H), 3.28-3.25 (dd, 4H), 2.96-2.94 (m, 2H), 2.88-2.86 (m, 2H), 2.81-2.79 (m, 2H), 2.70-2.68 (m, 2H), 2.64-2.62 (m, 2H), 2.56 (brs, 8H), 2.47 (brs, 2H), 1.86 (brs, 2H), 1.60 (brs, 2H), 1.39-1.37 (dd, 18H); 13C NMR (125 MHz, CDCl3): δ 178.1, 170.5, 170.4, 144.5, 129.9, 129.2, 115.1, 81.1, 80.9, 55.3, 55.0, 54.8, 52.0, 51.7, 51.3, 50.4, 48.6, 48.3, 48.22, 45.8, 30.9, 28.1, 24.4, 23.8, 22.8; HRMS (FAB) calculated for C30H54N5O4: 548.4176 [(M+H)+], measured value: 548.4172 [(M+H)+].

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 solvent was evaporated from the combined filtrate in vacuo
  5. customto give an oily residue, which

Sources & evidence

ORD record
ord-3e969b93b2134c8783899a81fe6e8bd2
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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