(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid → (S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

HRID 1055357Notes

Reaction equation

HRID 1055357 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 18599736(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid

Product 1

HCID 18599735(S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acidYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenoxy)-propionic acid (7.6 g, 23.3 mmol, leq) and 10% Pd/C (496 mg) in MeOH (215 mL) was hydrogenated at 1 atm for 2 h. After the theoretical uptake of hydrogen, the reaction mixture was filtered through Celite and washed with MeOH. The filtrate was concentrated and the residue was tritrurated with hexanes to give a solid that was filtered and washed with hexanes to give (S)-3-(2-amino-phenoxy)-2-tert-butoxycarbonylamino-propionic acid (3.8 g, 55%) as a white solid which was used without purification.

Workup

  1. filtrationAfter the theoretical uptake of hydrogen, the reaction mixture was filtered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated
  4. customto give a solid
  5. filtrationthat was filtered
  6. washwashed with hexanes

Sources & evidence

ORD record
ord-8def6ea3e7ad46c49c12222a6bfe8c04
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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