Tetrahydrofuran → 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide

HRID 1986427Notes

Reaction equation

HRID 1986427 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15]C(=O)OCC2C=CC=CC=2)=[C:11]([C:26]([N:28]([O:30][CH3:31])[CH3:29])=[O:27])[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O1CCCC1>C(O)C.[C].[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])=[CH:10][C:11]=1[C:26]([N:28]([O:30][CH3:31])[CH3:29])=[O:27]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86605626Benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}-2-{[methoxy(methyl)amino]carbonyl}phenyl)carbamate

Product 1

HCID 866056272-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamideYield 70.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of benzyl (4-{[tert-butyl(dimethyl)silyl]-oxy}-2-{[methoxy(methyl)amino]carbonyl}phenyl)carbamate (91 g, 0.20 mol) in ethanol (250 ml)-tetrahydrofuran (250 ml) was added 5% palladium-carbon (25 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 12 hrs. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was crystallized from n-hexane to give 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide (44 g, yield 70%) as white crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-fc2f525f274f4398bfc7d27012b8c77f
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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