Acetic Acid → HCID 54113518, compound

HRID 726791Notes

Reaction equation

HRID 726791 reaction equation
[C:1]([N:8]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(O)(=O)C.[H][H]>C(O)C.[Pd].[C]>[C:1]([N:8]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 18655318HCID 18655318, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54113518HCID 54113518, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Nα -Boc-4-Nitrophenyl-D-alanine (209 grams, 0.68 mole) was dissolved in 500 mL of ethyl alcohol and acidified with acetic acid (10 mL). To this was added 0.65 g of 10% Pd/carbon, and the mixture was hydrogenated at about room temperature using H2 at about 40 psi until the uptake of hydrogen had ceased (6 hours). The catalyst was removed by filtration, and the reaction products were concentrated under vacuum to yield a viscous oil that solidified upon trituration with petroleum ether. The amino acid was collected by filtration, washed with petroleum ether and dried to give 184 g of Nα -Boc-4-aminophenyl-D-alanine (0.659 mole, 97%) having [α]D =-40.2° (c=1.0 in EtOAc) and -23.4° (c=1.0 in MeOH); mp=128°-133° C.

Workup

  1. customwas hydrogenated at about room temperature
  2. custom(6 hours)
  3. customThe catalyst was removed by filtration
  4. concentrationthe reaction products were concentrated under vacuum
  5. customto yield a viscous oil that
  6. filtrationThe amino acid was collected by filtration
  7. washwashed with petroleum ether
  8. customdried

Sources & evidence

ORD record
ord-4331ec02e0e249f3af90a6e14bcf60ca
Source dataset
uspto-grants-1998_01
Patent number
US05710249

Reaction notes

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