Ethanol → HCID 58645826, compound

HRID 1765323Notes

Reaction equation

HRID 1765323 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[CH2:5]([O:12][C:13]([NH:15][CH:16]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=O)[CH2:17]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:27]([OH:29])[CH3:28]>>[CH2:5]([O:12][C:13]([NH:15][CH:16]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[CH:3][C:2]([O:29][CH2:27][CH3:28])=[O:1])[CH2:17]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 702Ethanol3×HCID 2723922Sodium ethoxideHCID 21107062HCID 21107062, compound

Product 1

HCID 58645826HCID 58645826, compound

Procedure

To a solution of triethyl phosphonoacetate (0.202 mL) in ethanol (2 mL) stirring at 0° C. under nitrogen was added a solution of sodium ethoxide in ethanol (21% by weight, 0.379 mL). After 1 h, a solution of 3-benzyloxycarbonylamino-1-oxo-1,2,3,4-tetrahydronaphthalene (100 mg) in ethanol (1 mL) was added. Upon completion of addition, the reaction mixture was stirred for 12 h and allowed to warm to room temperature. The reaction mixture was then quenched with 1.0 M aqueous hydrochloric acid solution and the ethanol was removed under reduced pressure. Water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated under vacuum to yield a residue. The residue was purified by reverse phase preparative HPLC (trifluoroacetic acid containing solvents were used) to obtain the title compound (55 mg) as a 2.7:1 mixture of the olefin isomers, which were separable but were combined for use in the next step.

Workup

  1. additionUpon completion of addition
  2. customThe reaction mixture was then quenched with 1.0 M aqueous hydrochloric acid solution
  3. customthe ethanol was removed under reduced pressure
  4. additionWater was added
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated under vacuum
  8. customto yield a residue
  9. customThe residue was purified by reverse phase preparative HPLC (trifluoroacetic acid containing solvents were used)

Sources & evidence

ORD record
ord-b44c7a8d890e40ada3b1ff4a423e2f8c
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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