Lawesson's reagent → HCID 11094084, 화합물

HRID 2306209노트

반응식

HRID 2306209 반응식
[Si:1]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][CH:25]=[C:26]2[N:29]2[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=O)[CH2:36][C:37]3[N:38]=[CH:39][N:40]([C:42]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:41]=3)[C:30]2=[O:62])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:72])=CC=1>C1COCC1>[Si:1]([O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][CH:25]=[C:26]2[N:29]2[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[S:72])[CH2:36][C:37]3[N:38]=[CH:39][N:40]([C:42]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:41]=3)[C:30]2=[O:62])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 10909025HCID 10909025, 화합물

생성물 1

HCID 11094084HCID 11094084, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

A mixture of (S)-N-{1-[7-(tert-butyldiphenylsilyloxy)naphthalen-1-yl]-2-oxopyrrolidin-3-yl}-2-[1-(triphenylmethyl)-1H-imidazol-4-yl]acetamide, as described above in Step D, (3.00 g, 3.61 mmol) and Lawesson's Reagent (728 mg, 1.80 mmol) in dry THF (45 mL), under argon, was heated to 45° C. for 90 min. The solvent was removed under reduced pressure and the residue was partitioned between saturated aqueous Na2CO3 (125 mL) and CH2Cl2 (300 mL). The aqueous layer was extracted further with CH2Cl2 (150 mL) and the combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—40% EtOAc—1% MeOH—0.1% NH4OH to yield the desired product.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous Na2CO3 (125 mL) and CH2Cl2 (300 mL)
  3. extractionThe aqueous layer was extracted further with CH2Cl2 (150 mL)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash column chromatography on silica
  8. washeluting with hexane—40% EtOAc—1% MeOH—0.1% NH4OH

출처 및 근거

ORD 기록
ord-a36db1d8128845e895c03962886e5867
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06441017B1

반응 노트

불러오는 중…