2-Bromothiazole → HCID 67269896, 화합물

HRID 1039726

반응식

HRID 1039726 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 67269896HCID 67269896, 화합물수율 83%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-788abf77555a4ba5957ce475d61de960
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552181B2

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