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

HRID 18970ノート

反応式

HRID 18970 の反応式
[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]

参加物

5

反応物 2

HCID 2734631(S)-2-((tert-Butoxycarbonyl)amino)-3-(furan-2-yl)propanoic acidHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-51ca3a4795d34c4db7cce5493b14e438
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

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