Methanamine, N-methoxy-, hydrochloride (1:1) → (2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-N-methoxy-N,2-dimethyl-propanamide

HRID 2070728Notes

Reaction equation

HRID 2070728 reaction equation
C([Mg]Cl)(C)C.[C:6]([Si:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:11][CH2:12][C@H:13]([CH3:18])[C:14](OC)=[O:15])([CH3:9])([CH3:8])[CH3:7].Cl.[CH3:32][O:33][NH:34][CH3:35]>O1CCCC1>[CH3:8][C:6]([Si:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[O:11][CH2:12][C@H:13]([CH3:18])[C:14]([N:34]([O:33][CH3:32])[CH3:35])=[O:15])([CH3:7])[CH3:9]

Participants

5

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 11302759(2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpropanoic Acid Methyl EsterHCID 178418918HCID 178418918, compound

Product 1

HCID 86663240(2S)-3-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-N-methoxy-N,2-dimethyl-propanamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of iso-propylmagnesium chloride (2M in tetrahydrofuran, 28 mL) was added dropwise to a stirred mixture of (2S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid, methyl ester (Eur. J. Org. Chem. 2006, 3645, 7.5 g), O,N-dimethylhydroxylamine hydrochloride (2.55 g) and tetrahydrofuran (65 mL) at 0° C. After completion the mixture was quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give the crude product as a solid (8.1 g).

Workup

  1. customAfter completion the mixture was quenched with sat. aqueous NH4Cl
  2. extractionextracted into ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7009caa6dbbf4392b17782cf4763d2a0
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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