tert-Butyl-5-((4-((4-(4-fluorobenzoyl)phenyl)ethynyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → Tert-butyl-5-(4-(4-(4-fluorobenzoyl)phenethyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710322Notes

Reaction equation

HRID 710322 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:40])[C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:28][CH:27]=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]>[Pd]>[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:40])[C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[CH:28][CH:27]=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

3

Reactant 1

HCID 131733936tert-Butyl-5-((4-((4-(4-fluorobenzoyl)phenyl)ethynyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 131733937Tert-butyl-5-(4-(4-(4-fluorobenzoyl)phenethyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of the product of Step E (0.06 g, 0.13 mmol) and 10% Pd/C (0.03 g) was stirred for 16 h under H2 the (balloon). The catalyst was removed by filtration through Celite pad and the filtrate evaporated to dryness to give the product (0.032 g; 53%) as pale paste. 1H-NMR (CDCl3) 1.4 (s, 3H); 1.41 (s, 3H); 1.45 (s, 9H); 1.92-1.98 (m, 2H); 2.5-2.56 (m, 2H); 2.89-2.97 (m, 4H); 3.65 (d, 2H, J=11.8 Hz); 3.86 (d, 2H, J=11.76 Hz); 4.95 (s, 1H), 7.08 (s, 4H); 7.14 (tr, 2H, J=8.64 Hz), 7.25 (d, 2H); 7.67 (d, 2H, J=8.17 Hz); 7.78-7.84 (m, 2H).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. customthe filtrate evaporated to dryness
  3. customto give the product (0.032 g; 53%) as pale paste

Sources & evidence

ORD record
ord-e26d75d93382419c9952274aa693299d
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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