Cesium carbonate → Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]malonate

HRID 1666986ノート

反応式

HRID 1666986 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][C:9]1[S:10][C:11]([CH:14]2[CH2:16][CH2:15]2)=[N:12][N:13]=1.[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([C:40]1[N:41]=[CH:42][NH:43][CH:44]=1)([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([C:40]1[N:41]=[CH:42][N:43]([CH2:8][C:9]2[S:10][C:11]([CH:14]3[CH2:16][CH2:15]3)=[N:12][N:13]=2)[CH:44]=1)([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:23])([CH3:19])([CH3:20])[CH3:18]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27576792-(Chloromethyl)-5-cyclopropyl-1,3,4-thiadiazoleHCID 178471441HCID 178471441、化合物

生成物 1

HCID 67443151Diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-[1-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylmethyl)-1H-imidazol-4-yl]malonate収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Together with 1.97 g (6.04 mmol) of cesium carbonate and 0.29 g (1.66 mmol) of 2-chloromethyl-5-cyclopropyl-1,3,4-thiadiazole, a solution of 0.60 g (1.51 mmol) of diethyl 2-(4-tert-butoxycarbonylaminobutyl)-2-(1H-imidazol-4-yl)malonate in 12 ml of DMF was heated at 75° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was taken up in ethyl acetate and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatographic purification of the residue on silica gel (CH2Cl2:MeOH:water:acetic acid 95:5:0.5:0.5) gave 0.145 g (18%) of the title compound.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the residue on silica gel (CH2Cl2:MeOH:water:acetic acid 95:5:0.5:0.5)

出典と根拠

ORDレコード
ord-264ef64331ce40d6b8eaf08f6d8f4d28
出典データセット
uspto-grants-2011_10
特許番号
US08044208B2

反応ノート

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