HCID 54294220, compound → HCID 14560589, compound

HRID 1647064Notes

Reaction equation

HRID 1647064 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.C(O)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

6

Reactant 2

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

Product 1

HCID 14560589HCID 14560589, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6386tert-ButanolSolvent

Procedure

(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-[4-[3-(1,1-dimethylethoxy)-3-oxo-1-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-28af36205a09429d874eb7aafbca8ec8
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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