N~2~-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-D-alaninamide → HCID 71280220, compound

HRID 245932Notes

Reaction equation

HRID 245932 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@@H:8]([C:10](=[O:15])N(OC)C)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([Mg]Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([CH3:9])[C:10](=[O:15])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 23537239N~2~-(tert-Butoxycarbonyl)-N-methoxy-N-methyl-D-alaninamideHCID 178418336HCID 178418336, compound

Product 1

HCID 71280220HCID 71280220, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottomed flask, [(R)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (300 mg, 1.29 mmol) was dissolved in THF (8 ml). The solution was cooled to −16° C. (NaCl/ice bath) and benzylmagnesium chloride (1.0 M in diethyl ether, 3.8 ml, 3.8 mmol) was added dropwise. After the addition, the reaction mixture was allowed to warm slowly to room temperature and stirred for 5.5 h. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc) to afford 353 mg (99%) of ((R)-1-methyl-2-oxo-3-phenyl-propyl)-carbamic acid tert-butyl ester as a colorless oil.

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc)

Sources & evidence

ORD record
ord-32fb9cf70cc14f718c5193c6bfeb201e
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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