(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate → tert-Butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

HRID 13011

Reaction equation

HRID 13011 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11](N(OC)C)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[Mg][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH3:10])[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178490745HCID 178490745, compound

Product 1

HCID 59339682tert-Butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-L-alaninamide (777 mg, 3.3 mmol) in dry THF (50 ml) was added a solution of bromo(3-methoxyphenyl)magnesium (1M in THF, 10 ml, 10 mmol). The mixture was stirred at r.t. for 5 h, then quenched with saturated aqueous NH4Cl (50 ml). After stirring for 30 min, the layers were separated, the aqueous layer extracted with ethyl acetate (50 ml). The combined organic layers were dried with Na2SO4, and the solvent was removed in vacuo. The subtitle compound was isolated by flash chromatography on silica gel (n-heptane/ethyl acetate, gradient from 20 to 50% ethyl acetate). Yield 471 mg (94%).

Workup

  1. customquenched with saturated aqueous NH4Cl (50 ml)
  2. stirringAfter stirring for 30 min
  3. customthe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate (50 ml)
  5. dry with materialThe combined organic layers were dried with Na2SO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f4472b8e8622454faf43aa67199a63c4
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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