Phenethylamine → methyl(2S)-2-({[benzyl(methyl)amino]carbonyl}amino)-3,3-dimethylbutanoate

HRID 1174222Notes

Reaction equation

HRID 1174222 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C@H:3]([NH:8][C:9]([O:11]C1C=CC([N+]([O-])=O)=CC=1)=O)[C:4]([O:6][CH3:7])=[O:5].C([CH2:30][NH2:31])C1C=CC=CC=1.[C:32]1([CH3:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:38]([N:31]([CH3:30])[C:9]([NH:8][C@@H:3]([C:2]([CH3:1])([CH3:21])[CH3:22])[C:4]([O:6][CH3:7])=[O:5])=[O:11])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 1001PhenethylamineHCID 1140TolueneHCID 58412867methyl(2S)-3,3-dimethyl-2-{[(4-nitrophenoxy)carbonyl]amino}butanoate

Product 1

HCID 67408150methyl(2S)-2-({[benzyl(methyl)amino]carbonyl}amino)-3,3-dimethylbutanoateYield 65%

Conditions

Temperature
80 °C

Procedure

A solution containing the product from Example 63A (0.075 g, 0.242 mmol) in toluene (0.5 mL) was treated with N-benzylmethylamine (0.035 mL, 2.71 mmol), and the mixture was stirred at 80° C. for 1 hour. The reaction was partitioned between ethyl acetate and 10% Na2CO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in dichloromethane to give the title compound (0.046 g, 65% yield).

Workup

  1. customThe reaction was partitioned between ethyl acetate and 10% Na2CO3
  2. washthe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-a2e8152a43454a0c9efcc2e3424446a4
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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