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

HRID 18970노트

반응식

HRID 18970 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-51ca3a4795d34c4db7cce5493b14e438
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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