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

HRID 337048Notes

Reaction equation

HRID 337048 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-94c50b92594242a9b7544da2fa1cd0d4
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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