Magnesium → HCID 77506189, compound

HRID 1712463Notes

Reaction equation

HRID 1712463 reaction equation
[CH3:1][O:2][C:3]1[CH:55]=[CH:54][CH:53]=[CH:52][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][CH:32]2[CH2:37][N:36](S(C3C=CC(C)=CC=3)(=O)=O)[C:35]3[CH:48]=[CH:49][CH:50]=[CH:51][C:34]=3[O:33]2)=[CH:13][CH:12]=1.[Mg]>CO.C(OCC)(=O)C>[O:33]1[C:34]2[CH:51]=[CH:50][CH:49]=[CH:48][C:35]=2[NH:36][CH2:37][CH:32]1[CH2:31][O:30][CH:18]1[CH:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C:4]3[CH:52]=[CH:53][CH:54]=[CH:55][C:3]=3[O:2][CH3:1])=[CH:12][CH:13]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1

Participants

5

Reactant 2

HCID 5462224Magnesium2×HCID 77506156HCID 77506156, compound

Product 1

HCID 77506189HCID 77506189, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.66 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[4-toluene-4-sulphonyl-3,4-dihydro-2H-benzo[1,4]oxazin-2(R,S)-ylmethoxy]piperidine-1-carboxylate in 10 ml of methanol is treated in an ultrasound bath in the presence of 0.5 g of magnesium turnings over 30 minutes. The reaction mixture is decantered off from the magnesium, diluted with ethyl acetate, washed with 1N HCl (2×), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (1:2 EtOAc-heptane); Rt=5.62.

Workup

  1. washwashed with 1N HCl (2×)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6fbc7937fa764883a061dfd2efefbe25
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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