Water → 3-(4-Nitrophenyl)-2(S)-(3-oxo-7-oxaspiro[3.5]non-1-en-1ylamino)propionic acid ethyl ester

HRID 966408Notes

Reaction equation

HRID 966408 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:18])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[C:19](=[O:22])([O-])[O-].[K+].[K+].[OH2:25]>ClCCl>[CH2:2]([O:4][C:5](=[O:18])[C@@H:6]([NH:7][C:8]1[C:9]2([CH2:14][CH2:13][O:25][CH2:11][CH2:10]2)[C:19](=[O:22])[CH:6]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 6453710Ethyl 4-nitro-3-phenyl-L-alaninate monohydrochloride

Product 1

HCID 865917993-(4-Nitrophenyl)-2(S)-(3-oxo-7-oxaspiro[3.5]non-1-en-1ylamino)propionic acid ethyl esterYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitro-(L)-phenylalanine ethyl ester hydrochloride (28.6 g) was suspended in dichloromethane (290 mL) to which a solution of potassium carbonate (8.0 g) in water (100 mL) was added slowly with stirring. After removal of the aqueous phase, the organic layer was washed with water (2×50 mL) and then dried (Na2SO4). Following removal of the drying agent, solid Intermediate 7 (16.1 g) was added portion-wise to the stirred dichloromethane solution. The resulting mixture was left to stir-out overnight at 20-25° C. under nitrogen. The solution was sequentially washed with 5% aqueous sodium bicarbonate (100 mL), and water (2×50 mL), then dried (Na2SO4) prior to solvent removal in vacuo which afforded the title compound as an off-white foam (38.6 g, 99.2% yield).

Workup

  1. additionwas added slowly
  2. customAfter removal of the aqueous phase
  3. washthe organic layer was washed with water (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. customremoval of the drying agent, solid Intermediate 7 (16.1 g)
  6. additionwas added portion-wise to the stirred dichloromethane solution
  7. waitThe resulting mixture was left
  8. stirringto stir-out overnight at 20-25° C. under nitrogen
  9. washThe solution was sequentially washed with 5% aqueous sodium bicarbonate (100 mL), and water (2×50 mL)
  10. dry with materialdried (Na2SO4)
  11. customto solvent removal in vacuo which

Sources & evidence

ORD record
ord-84b8b98e161140a6990ef040cfe852fc
Source dataset
uspto-grants-2005_10
Patent number
US06951943B2

Reaction notes

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