Diethyl Ether → HCID 89303295, compound

HRID 1523104Notes

Reaction equation

HRID 1523104 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][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[CH:34][CH:33]=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]([CH3:29])([CH3:30])[CH3:28])=[O:25])[CH2:15][CH2:14][CH2:13][N:12]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([NH2:38])=[CH:36][CH:37]=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 71133754HCID 71133754, compound

Product 1

HCID 89303295HCID 89303295, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound (7) (1.22 g, 2.16 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 combined filtrate was evaporated in vacuo to give an oily residue, which was then treated with Et2O to obtain an off-white solid of compound (9) (1.13 g, 98% yield). 1H NMR (500 MHz, CDCl3): δ 7.07-7.06 (dd, 2H), 6.67-6.65 (dd, 2H), 3.39 (s, 4H), 3.30-3.14 (m, 4H), 3.12-3.01 (m, 4H), 2.77-2.75 (m, 2H), 2.70-2.42 (m, 8H), 1.96 (brs, 2H), 1.80 (brs, 2H), 1.46-1.45 (dd, 18H); 13C NMR (125 MHz, CDCl3): δ 171.1, 170.7, 145.6, 130.7, 127.6, 115.0, 81.6, 81.2, 57.9, 55.4, 54.7, 54.1, 51.6, 51.5, 49.8, 49.7, 49.4, 46.0, 28.2, 24.3, 24.1, 22.5; HRMS (FAB) calculated for C29H52N5O4: 534.4019 [(M+H)+], measured value: 534.4024 [(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 combined filtrate was evaporated in vacuo
  5. customto give an oily residue, which

Sources & evidence

ORD record
ord-18c0588d6942454283e4a584610f091f
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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