Lawesson's reagent → HCID 11094084、化合物

HRID 2306209ノート

反応式

HRID 2306209 の反応式
[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

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 10909025HCID 10909025、化合物

生成物 1

HCID 11094084HCID 11094084、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a36db1d8128845e895c03962886e5867
出典データセット
uspto-grants-2002_08
特許番号
US06441017B1

反応ノート

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