Acetyl chloride → 1-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 72112

반응식

HRID 72112 반응식
[Cl:1][C:2]1[C:3]([OH:12])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C2C(=CC=CC=2)N=CC=1.[N+]1([O-])C2C(=CC=CC=2)[N+]([O-])=CC=1.C(Cl)(=O)C.O[C@@H:40]1[CH2:44][N:43]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:42]([C:52]([O:54][CH3:55])=[O:53])[CH2:41]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:3]([O:12][C@H:40]2[CH2:44][N:43]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:42]([C:52]([O:54][CH3:55])=[O:53])[CH2:41]2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

참가 물질

9

반응물 7

HCID 6367Acetyl chlorideHCID 7045QuinoxalineHCID 11776TriphenylphosphineHCID 3027053-chloro-1H-quinoxalin-2-oneHCID 5363146Diisopropyl azodicarboxylateHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterHCID 178526279HCID 178526279, 화합물

생성물 1

HCID 580914191-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

A solution of 3-chloroquinoxalin-2-ol (1.44 g, 7.97 mmol) (Yusuf Ahmad et al., Quinoxaline Derivatives, XI. The Reaction of Quinoxaline 1,4-Dioxide and Some of Its Derivatives with Acetyl Chloride, 38(12) J. ORG. CHEM. 2176 (1973)) and 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.05 g, 8.37 mmol) in THF (190 ml) was cooled to 0° C., then treated with PPh3 (2.51 g, 9.57 mmol). DIAD (1.86 ml, 9.57 mmol) was added dropwise, and the mixture was stirred at 20° C. for 1 hour. After evaporation of the volatiles, the residue was purified on SiO2 (gradient elution, 0-70% EtOAc/petroleum ether) to afford the title compound (2.5 g, 77%). LCMS (ES+) m/z 408 (M+H)+

후처리

  1. customAfter evaporation of the volatiles
  2. customthe residue was purified on SiO2 (gradient elution, 0-70% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-d8e46f6718ea456c8e8983061f4f0371
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828930B2

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