(S)-2-((tert-Butoxycarbonyl)amino)-3-(furan-2-yl)propanoic acid → (αS)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]tetrahydro-2-furanpropanoic acid

HRID 18970Notes

Reaction equation

HRID 18970 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt]=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:18][CH2:17][CH2:16][O:15]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2734631(S)-2-((tert-Butoxycarbonyl)amino)-3-(furan-2-yl)propanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 60096939(αS)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]tetrahydro-2-furanpropanoic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a Parr shaker bottle was placed (S)-2-t-butoxycarbonylamino-3-furan-2-yl-propionic acid (3.88 g, 15.22 mmol), platinum oxide (200 mg) and ethyl acetate (40 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 5 h. The reaction was then filtered through a pad of celite and washed with ethyl acetate and concentrated in vacuo to afford (S)-2-t-butoxycarbonylamino-3-(tetrahydro-furan-2-yl)-propionic acid (3.60 g, 91%) as a yellow oil: LR-ES-MS m/z calculated for C12H21NO5 [M]+ 259, observed [M+H]+ 260.

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washwashed with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51ca3a4795d34c4db7cce5493b14e438
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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