Sodium ethoxide → HCID 18321616, compound

HRID 1867589Notes

Reaction equation

HRID 1867589 reaction equation
[O-]CC.[Na+].[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C@H:22]([C:30](OC)=[O:31])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C>[CH2:23]([CH:22]1[NH:21][C:19](=[O:20])[N:18]([CH:15]2[CH2:16][CH2:17][N:12]([CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:13][CH2:14]2)[C:30]1=[O:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 7586306HCID 7586306, compound

Product 1

HCID 18321616HCID 18321616, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (0.1301 mL, 1.66 mmol, 21% wt.) was added to a solution of methyl N-{[(1-benzylpiperidin-4-yl)amino]carbonyl}phenylalaninate (546 mg, 1.38 mmol) in ethanol (715 mL) at 0° C. and then warmed to ambient temperature. The reaction was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to give the title compound (490 mg). MS 364.2 (M+1)

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-beb85712147546e181b46c6a8ca03c57
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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