(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate → (S)-tert-butyl 3-oxo-4-phenylbutan-2-ylcarbamate

HRID 473441Notes

Reaction equation

HRID 473441 reaction equation
CON(C)[C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].C([Mg]Cl)(C)C.[CH2:22]([Mg]Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[O:15]=[C:4]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6]

Participants

5

Reactant 3

HCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178418336HCID 178418336, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 59634589(S)-tert-butyl 3-oxo-4-phenylbutan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (1.16 g, 5 mmol) in THF (10 mL) was cooled to −15° C. and slowly charged with isopropylmagnesium chloride (2.0M, 2.37 mL, 0.95 eq). After a clear solution was obtained, benzylmagnesium chloride (1.0M, 4.99 mL, 1.0 eq) was added dropwise with stirring at rt overnight. The reaction mixture was quenched with NH4Cl solution and extracted with EtOAc (10 mL×2). The combined organic layers were washed with water, brine, dried over sodium sulfate before being filtered, concentrated to give a white solid as (S)-tert-butyl 3-oxo-4-phenylbutan-2-ylcarbamate. Mass Spectrum (ESI) m/e=264 (M+1).

Workup

  1. customAfter a clear solution was obtained
  2. customThe reaction mixture was quenched with NH4Cl solution
  3. extractionextracted with EtOAc (10 mL×2)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationbefore being filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34d9df167d8a4ca9b882f9722d3187ba
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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