Potassium Carbonate → methyl (5E,8S)-8-[(tert-butoxycarbonyl)amino]-7-oxo-9-phenyl-non-5-enoate

HRID 638833Notes

Reaction equation

HRID 638833 reaction equation
O=[CH:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:19](=[O:27])[CH2:20]P(=O)(OC)OC)=[O:16])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>C(O)C>[C:10]([O:14][C:15]([NH:17][C@@H:18]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:19](=[O:27])/[CH:20]=[CH:2]/[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 554053Pentanoic acid, 5-oxo-, methyl esterHCID 7021151Dimethyl((3S)-4-phenyl-3-(Boc-amino)-2-oxobutyl)phosphonate

Product 1

HCID 86614843methyl (5E,8S)-8-[(tert-butoxycarbonyl)amino]-7-oxo-9-phenyl-non-5-enoateYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of aldehyde (methyl 5-oxopentanoate) (1) (3.0 g, 23.1 mmol), in absolute ethanol (100 mL) is added, under stirring, to a solution of dimethyl (3S)-3-[(tert-butoxycarbonyl)amino]-2-oxo-4-phenylbutyl-phosphonate (2) (8.58 g, 23.1 mmol) and K2CO3 (3.2 g, 23.1 mmol), dried at 75° C. for 12 hours, in absolute ethanol (200 mL). The mixture is then stirred at room temperature for 16 hours, the solid residue is filtered off and the solution neutralised with glacial acetic acid. The solvent is removed under reduced pressure and the residue partitioned between ethyl acetate and a saturated solution of NaHCO3. The aqueous phase is extracted with ethyl acetate (2×50 mL) and the pooled organic phases are washed with a saturated NaCl solution and dried over anhydrous Na2SO4. The solvent is removed by distilling under reduced pressure and the product purified by means of flash chromatography on a silica gel column by using a 1:1 mixture of ethyl ether and petroleum ether as eluant. 6.8 g (79%) of a colourless oil are obtained.

Workup

  1. dry with materialdried at 75° C. for 12 hours, in absolute ethanol (200 mL)
  2. filtrationthe solid residue is filtered off
  3. customThe solvent is removed under reduced pressure
  4. customthe residue partitioned between ethyl acetate
  5. extractionThe aqueous phase is extracted with ethyl acetate (2×50 mL)
  6. washthe pooled organic phases are washed with a saturated NaCl solution
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent is removed
  9. distillationby distilling under reduced pressure
  10. customthe product purified by means of flash chromatography on a silica gel column
  11. additiona 1:1 mixture of ethyl ether and petroleum ether as eluant

Sources & evidence

ORD record
ord-2458a338e99d4e979d7641fbbd5f49af
Source dataset
uspto-grants-2010_04
Patent number
US07691818B2

Reaction notes

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