HCID 54294220, compound → HCID 14560589, compound

HRID 1721239Notes

Reaction equation

HRID 1721239 reaction equation
C1(C([O:14][C:15](=[O:41])[C@@H:16]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][CH:19]=2)C2C=CC=CC=2)C=CC=CC=1.[H][H]>C(O)(C)(C)C.[Pd]>[CH3:39][C:37]([CH3:40])([O:36][C:34]([NH:33][C@@H:16]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][CH:19]=1)[C:15]([OH:41])=[O:14])=[O:35])[CH3:38]

Participants

5

Reactant 2

HCID 54294220HCID 54294220, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 14560589HCID 14560589, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6386tert-ButanolSolvent

Procedure

(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-[4-[3-(1,1-dimethylethoxy)-3-oxo-l-propenyl]phenyl]propanoic acid diphenylmethyl ester (1.6 g. 2.8 mmol) and 10% Pd/C (300 mg) in t-butanol (20 mL) was blanketed with hydrogen (1 atm). To prevent the solvent from freezing, a warm water bath (40° C.) was used to heat the reaction mixture. Upon the consumption of 2 equivalents of hydrogen, the mixture was filtered through celite. The celite pad was washed with ethanol (50 mL) and the filtrates combined and concentrated. The residue was purified by recrystallization from hexanes to give (S)-2-[[(1,1-dimethylethoxy) carbonyl]amino]-3-[4-[3-(1,1-dimethylethoxy)3-oxopropyl]phenyl]propanoic acid (1.0 g, 2.6 mmol) in 94% yield. mp. 88.5°-90° C., [α]D +21.2° (0.90% in ethanol).

Workup

  1. customa warm water bath (40° C.) was used
  2. temperatureto heat the reaction mixture
  3. filtrationthe mixture was filtered through celite
  4. washThe celite pad was washed with ethanol (50 mL)
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from hexanes

Sources & evidence

ORD record
ord-2ba03f0db3d349ac9398bbfa3c539507
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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