HCID 24903490, compound → HCID 68618190, compound

HRID 1433753Notes

Reaction equation

HRID 1433753 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 24903490HCID 24903490, compound

Product 1

HCID 68618190HCID 68618190, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2R)-tert-butoxycarbonylamino-(4-nitro-phenyl)-acetic acid (350 mg, <1.18 mmol) in absolute ethanol (15 mL) was added a small amount of 10% palladium on carbon and the mixture stirred under an atmosphere of hydrogen for 16 hours. The reaction mixture was filtered through a pad of Celite and the Celite eluted with absolute ethanol. The filtrate was concentrated in vacuo then purified by chromatography over silica gel gradient eluted between 0 and 7% v/v methanol in dichloromethane. (2R)-(4-Amino-phenyl)-tert-butoxycarbonylamino-acetic acid was obtained as a yellow oil (146 mg, 46%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe Celite eluted with absolute ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthen purified by chromatography over silica gel gradient
  5. washeluted between 0 and 7% v/v methanol in dichloromethane

Sources & evidence

ORD record
ord-20a272dbd164413faca75f28a8074d34
Source dataset
uspto-grants-2009_11
Patent number
US07612212B2

Reaction notes

Loading…