tert-Butyl-5-((4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfam-oyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → tert-Butyl 5-(4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfamoyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710343Notes

Reaction equation

HRID 710343 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:36])(=[O:35])[NH:25][CH:26]3[CH2:31][CH2:30][CH:29]4[CH2:32][CH:27]3[C:28]4([CH3:34])[CH3:33])=[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]>[CH3:33][C:28]1([CH3:34])[CH:27]2[CH2:32][CH:29]1[CH2:30][CH2:31][CH:26]2[NH:25][S:24]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][CH2:16][C:8]2([NH:7][C:6](=[O:37])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][O:12][C:11]([CH3:14])([CH3:15])[O:10][CH2:9]2)=[CH:23][CH:22]=1)(=[O:36])=[O:35]

Participants

4

Reactant 1

HCID 131733945tert-Butyl-5-((4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfam-oyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 86661778tert-Butyl 5-(4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfamoyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step B (0.075 g, 0.14 mmol) and 10% Pd/C (0.04 g) in EtOH (10 ml) was stirred for 16 h under H2. The catalyst was removed by filtration through Celite pad and the filtrate was evaporated to dryness, to give the desired product (0.067 g; 87%), as creamy gum. 1H-NMR (CDCl3) 0.84 (s, 3H); 1.09 (s, 3H); 1.44 (m, 10H); 1.85 (m, 6H); 2.10 (m, 1H); 2.29 (m, 1H); 2.67 (m, 2H); 2.90 (m, 2H); 3.66 (m, 2H); 3.82 (m, 2H); 4.33 (s, 1H); 5.10 (s, 1H); 7.32 (m, 2H); 7.74 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-b4f78288837f42cda2e16328a2eea968
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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