(R)-Toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester → [2(R)-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-[1,1-dimethyl-2-(4-nitro-phenyl)-ethyl]-amine

HRID 495716Notes

Reaction equation

HRID 495716 reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C@H:7]([C:20]1[CH:21]=[N:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:8]OS(C1C=CC(C)=CC=1)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[NH2:29][C:30]([CH3:42])([CH3:41])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1>CS(C)=O>[C:1]([Si:5]([CH3:27])([CH3:28])[O:6][C@H:7]([C:20]1[CH:21]=[N:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:8][NH:29][C:30]([CH3:42])([CH3:41])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 12972452(R)-Toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl esterHCID 13897642HCID 13897642, compound

Product 1

HCID 20826856[2(R)-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-[1,1-dimethyl-2-(4-nitro-phenyl)-ethyl]-amineYield 63.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (R)-toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester (12.0 g) and 11.4 g of 2-amino-2-methyl-1-(4-nitrophenyl)propane (prepared by the method described in J. Milecki, et al. J. Med. Chem., 30, 1563 (1987)) in DMSO (30 mL) was stirred at 100° C. for 48 h. The reaction solution was partitioned between ethyl ether/water, the resulting organic layer washed with water (3×), brine, dried over sodium sulfate and concentrated in vacuo to afford an oil. Flash chromatography on silica gel (20% to 50% ethyl acetate/hexanes) afforded 8.0 g of the title compound (I-2f) as a golden oil.

Workup

  1. customThe reaction solution was partitioned between ethyl ether/water
  2. washthe resulting organic layer washed with water (3×), brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford an oil

Sources & evidence

ORD record
ord-6389954421314fd290cdc59f0057c520
Source dataset
uspto-grants-2005_09
Patent number
US06939867B2

Reaction notes

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