2-Bromothiazole → HCID 67269896、化合物

HRID 1697256

反応式

HRID 1697256 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[Si:12]([O:19][C@H:20]([CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])/[CH:21]=[N:22]/[S@:23]([C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CCOCC>[Si:12]([O:19][C@H:20]([CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[C@@H:21]([NH:22][S@:23]([C:25]([CH3:26])([CH3:27])[CH3:28])=[O:24])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 764302-BromothiazoleHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamideHCID 178418339Butyllithium

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-butyllithium (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-94bd15697fa24e409acd93184e48aa52
出典データセット
uspto-grants-2012_04
特許番号
US08163909B2

関連ノート

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