HCID 131733952, compound → HCID 131733953, compound

HRID 710356Notes

Reaction equation

HRID 710356 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]#[C:27][C:28]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:20][CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:20][CH:19]=2)[CH2:9][O:10][C:11]([CH3:15])([CH3:14])[O:12][CH2:13]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 131733952HCID 131733952, compound

Product 1

HCID 131733953HCID 131733953, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step B (0.07 g, 0.13 mmol), and 10% Pd/C (0.04 g) was stirred for 36 h in EtOH (5 ml) under H2. The catalyst was removed by filtration through Celite pad and the filtrate as evaporated to dryness to give the title product (0.043 g; 60%), as colourless paste. 1H-NMR (CDCl3) 1.35 (s, 9H); 1.39 (s, 3H); 1.41 (s, 3H); 1.48-1.49 (m, 20H); 2.15 (d, 2H, J=11.22 Hz); 2.49-2.45 (m, 2H); 3.64 (d, 2H, J=11.73 Hz); 3.86 (d, 2H, J=11.7 Hz); 3.94 (m, 2H); 4.95 (s, 1H); 6.78 (d, 2H, J=8.58 Hz); 7.04 (d, 2H, J=8.55 Hz).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. customthe filtrate as evaporated to dryness

Sources & evidence

ORD record
ord-1ce140f5d16748f0a77a24abb5caed78
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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