HCID 14326881, compound → HCID 14326871, compound

HRID 2232887Notes

Reaction equation

HRID 2232887 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([NH:18][C:19](=O)[CH2:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](OC(C)(C)C)=[O:12])[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[H][H]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([NH:18][CH2:19][CH2:20][CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14326881HCID 14326881, compoundHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 14326871HCID 14326871, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxy-α-[(1-oxo-3,3-diphenylpropyl)amino]benzenepropionic acid, 1,1-dimethylethyl ester (1 eq, 1 mmole, 470 mg) was added portionwise to a mixture of lithium aluminum hydride (3 mmole, 3 ml of 1M in tetrahydrofuran) in tetrahydrofuran (5 ml) at 0° C. under argon. After the addition and the cessation of hydrogen evolution, the mixture was brought to reflux. The mixture was refluxed overnight, cooled to room temperature and quenched with solid sodium sulfate.10 water. The solids were removed by filtration through Celite, and the solvent was evaporated in vacuo to yield an oil which crystallized upon standing. The crystals were washed with hexanes/ether, collected, and dried to afford 299.9 mg of the title compound, melting point 89°-91° C.

Workup

  1. additionAfter the addition
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed overnight
  4. customquenched with solid sodium sulfate
  5. customThe solids were removed by filtration through Celite
  6. customthe solvent was evaporated in vacuo
  7. customto yield an oil which
  8. customcrystallized
  9. washThe crystals were washed with hexanes/ether
  10. customcollected
  11. customdried

Sources & evidence

ORD record
ord-78776a70aecc49e5b75363688d9bb081
Source dataset
uspto-grants-1988_11
Patent number
US04788010

Reaction notes

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