2-Bromothiazole → HCID 67269896、化合物

HRID 1039726

反応式

HRID 1039726 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Si:7]([O:14][C@H:15]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])/[CH:16]=[N:17]/[S@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>CCOCC>[Si:7]([O:14][C@H:15]([CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[C@@H:16]([NH:17][S@:18]([C:20]([CH3:21])([CH3:22])[CH3:23])=[O:19])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:9])[CH3:8]

参加物

4

反応物 2

HCID 764302-BromothiazoleHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamide

生成物 1

HCID 67269896HCID 67269896、化合物収率 83%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 2-bromothiazole (7.9 ml, 89 mmol) in 200 mL ether was cooled to −78° C. and treated with a solution of n-butylithium (36 ml, 89 mmol) (2.5N in hexanes). After stirring for 30 minutes the reaction mixture was slowly added to a cooled (−78° C.) suspension of (S,E)-N-((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (25.000 g, 59 mmol) in 100 mL ether. The reaction mixture was allowed to stir at −78° C. for one hour. The reaction mixture was quenched with MeOH and saturated NH4Cl solution. The organic solution was washed with water, brine, dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatography gave (S)-N-((1R,2S)-2,3-bis(tert-butyldimethylsilyloxy)-1-(thiazol-2-yl)propyl)-2-methylpropane-2-sulfinamide (24.81 g, 83% yield).

後処理

  1. additionwas slowly added to
  2. temperaturea cooled
  3. stirringto stir at −78° C. for one hour
  4. customThe reaction mixture was quenched with MeOH and saturated NH4Cl solution
  5. washThe organic solution was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by column chromatography

出典と根拠

ORDレコード
ord-788abf77555a4ba5957ce475d61de960
出典データセット
uspto-grants-2013_10
特許番号
US08552181B2

関連ノート

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