Diethyl Malonate → Diethyl 2-(5-(5-((S)-2-(tert-butoxycarbonylamino)-3-(4-(trifluoromethyl)phenyl)propyl-boc-amino)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)malonate

HRID 2075316ノート

反応式

HRID 2075316 の反応式
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].F[C:15]1[CH:16]=[C:17]([C:24]2[S:28][C:27]([N:29]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:30][C@@H:31]([NH:43][C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=3)=[N:26][N:25]=2)[CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22]>O1CCOCC1>[C:46]([O:45][C:44]([NH:43][C@@H:31]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:38]=1)[CH2:30][N:29]([C:51]([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52])[C:27]1[S:28][C:24]([C:17]2[CH:18]=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[C:15]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:16]=2)=[N:25][N:26]=1)=[O:50])([CH3:47])([CH3:48])[CH3:49]

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 57991896tert-Butyl (S)-1-(5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

生成物 1

HCID 57991921Diethyl 2-(5-(5-((S)-2-(tert-butoxycarbonylamino)-3-(4-(trifluoromethyl)phenyl)propyl-boc-amino)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)malonate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

Diethyl malonate (2.83 mL, 18.7 mmol) in 30 mL of 1,4-dioxane was added to sodium hydride (0.748 g, 60% dispersion in mineral oil, 18.7 mmol) in 10 mL of 1,4-dioxane at room temperature under nitrogen. The mixture became a clear solution within 5 minutes. The mixture was stirred for another 15 minutes followed by addition of the tert-butyl (S)-1-(5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate as described in Schemes 1a and 1b (3.0 g, 4.7 mmol). After overnight stirring, the solvent was removed. The residue was partitioned between EtOAc and saturated NH4Cl. The combined organic portions were washed with brine and dried over sodium sulfate. The crude product was used in the following reaction without purification.

後処理

  1. customwithin 5 minutes
  2. stirringAfter overnight stirring
  3. customthe solvent was removed
  4. customThe residue was partitioned between EtOAc and saturated NH4Cl
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe crude product was used in the following reaction without purification

出典と根拠

ORDレコード
ord-0a7291e03b914f87b6841104c51b22d9
出典データセット
uspto-grants-2011_04
特許番号
US07919504B2

反応ノート

読み込み中…