L-Aspartic Acid → (S)-tert-Butyl (2,5-dioxotetrahydrofuran-3-yl)carbamate
반응식
N[C@H](C(O)=O)CC(O)=O.N[C@H](C([O-])=O)CC([O-])=O.[C:19]([NH:26][C@H:27]([C:32]([O-:34])=[O:33])[CH2:28][C:29]([O-:31])=O)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(OC(=O)C)(=O)C>>[C:22]([O:21][C:19]([NH:26][C@@H:27]1[C:32](=[O:33])[O:34][C:29](=[O:31])[CH2:28]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]참가 물질
실험 절차
Due to its low cost, L aspartic acid appears to be the most attractive starting material for the preparation of (S)-3-amino-1-substituted-pyrrolidines. The literature method from L-aspartate (D. T. Witiak, loc. cit.) involves treatment of N-boc-L-aspartate with acetic anhydride to give (S)-3-(tert butoxycarbonylamino)succinic anhydride followed by addition of a primary amine and ring closure with heat to give the succinimide, (S)-3-(tert-butoxycarbonylamino)-1-substituted pyrrolidine-2,5-dione. The latter is then reduced and deblocked to give the 1-substituted-3-aminopyrrolidine in low overall yield. From our experience with this method some racemization takes place when the blocking group is p-toluenesulfonyl(tosyl) and the primary amine is benzylamine.
출처 및 근거
- ORD 기록
- ord-3a658f1e9b524a8bb8c6d29e6786a799
- 출처 데이터셋
- uspto-grants-1993_01
- 특허 번호
- US05177217
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