1,4-Dibromobutane → N-(4-Bromo-butyl)-2-(4-fluoro-phenylsulfanyl)-N-trityloxy-acetamide

HRID 1716319ノート

反応式

HRID 1716319 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([NH:12][O:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:39][CH2:40][CH2:41][CH2:42][CH2:43]Br>CN(C=O)C.CCOC(C)=O>[Br:39][CH2:40][CH2:41][CH2:42][CH2:43][N:12]([O:13][C:14]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:10](=[O:11])[CH2:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

参加物

6

反応物 3

HCID 80561,4-DibromobutaneHCID 10796Cesium carbonateHCID 866199392-(4-Fluoro-phenylsulfanyl)-N-trityloxy-acetamide

生成物 1

HCID 86619940N-(4-Bromo-butyl)-2-(4-fluoro-phenylsulfanyl)-N-trityloxy-acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-(4-fluoro-phenylsulfanyl)-N-trityloxy-acetamide (132.1 mg, 0.228 mmol) from step C and Cs2CO3 (125.6 mg, 0.385 mmol) in anhydrous DMF (3 mL) was added 1,4-dibromo-butane (0.2 ml, 364.8 mg) in one portion and the resulting solution was warmed to 60° C. After TLC indicated the completion of the reaction (<30 min), the reaction mixture was diluted with EtOAc and washed sequentially with water and saturated NaCl solution. The organic phase was then dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a crude material, which was then used in next step without further purification.

後処理

  1. customthe completion of the reaction (<30 min)
  2. washwashed sequentially with water and saturated NaCl solution
  3. dry with materialThe organic phase was then dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6d4ecc6ee2ce4d8ba6bbc64b3c4449ab
出典データセット
uspto-grants-2010_09
特許番号
US07803793B2

反応ノート

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