Hydrochloric Acid → (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-aminophenyl)propanoate

HRID 2197390Notes

Reaction equation

HRID 2197390 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=3)[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[H][H]>C1COCC1.[Pd]>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=3)[C:20]([O:22][CH3:23])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14284321(S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-nitrophenyl)propanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 14284323(S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-aminophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a hydrogenation reactor, (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-nitrophenyl)propanoate (3B; 25 g, 56 mmol) was dissolved in THF (200 mL), and 15 mL of 4N HCl was added to the reaction mixture. Then, 10% Pd/C (2.5 g) was added to the reaction mixture. Hydrogen was introduced into the reactor until pressure reached 4 MPa. The reaction was stirred at room temperature for 1 hour. The catalyst was removed by filtration and washed with THF. The pH of the solution was adjusted to about 7 by adding saturated NaHCO3 (aq) while the solution was on an ice bath. The organic layer was separated, and the aqueous layer was washed with CH2Cl2 (2×15 mL). The combined organic fractions were dried with anhydrous Na2SO4 to give a solution of (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-aminophenyl)propanoate 3C. The solution was used directly in step 3.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with THF
  3. additionby adding saturated NaHCO3 (aq) while the solution
  4. customwas on an ice bath
  5. customThe organic layer was separated
  6. washthe aqueous layer was washed with CH2Cl2 (2×15 mL)
  7. dry with materialThe combined organic fractions were dried with anhydrous Na2SO4

Sources & evidence

ORD record
ord-25bb0f63de54456aa4244a404b4c65d6
Source dataset
uspto-grants-2012_12
Patent number
US08338565B2

Reaction notes

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