Ethyl Acetate → Tert-butyl N-[3-oxo-3-(1,3-thiazol-2-YL)propyl]carbamate

HRID 2179950

반응식

HRID 2179950 반응식
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C([Li])CCC.[CH3:12][C:13]([O:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21](NCOC)=[O:22])([CH3:15])[CH3:14].C(OCC)(=O)C>O1CCCC1.CCCC(C)C>[CH3:15][C:13]([O:16][C:17](=[O:27])[NH:18][CH2:19][CH2:20][C:21](=[O:22])[C:2]1[S:3][CH:4]=[CH:5][N:6]=1)([CH3:12])[CH3:14]

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 764302-BromothiazoleHCID 86584230[2-(Methoxymethyl-carbamoyl)-ethyl]-carbamic acid tert-butyl esterHCID 178418339Butyllithium

생성물 1

HCID 69802122Tert-butyl N-[3-oxo-3-(1,3-thiazol-2-YL)propyl]carbamate수율 67.1%

시약·촉매·용매 2

HCID 78922-Methylpentane용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 2-bromothiazole (5.035 g, 30.7 mmol) in dry tetrahydrofuran (125 ml) at −78° C. under nitrogen was added a solution of n-butyllithium in hexanes (1.6 M, 17.6 ml, 28.2 mmol) over a period of 30 minutes, followed by a solution of [3-(methoxymethylamino)-3-oxopropyl]carbamic acid 1,1-dimethylethyl ester (2.976 g, 12.8 mmol) in dry tetrahydrofuran (30 ml) added over 30 minutes. The reaction mixture was allowed to warm up to 0° C., quenched with saturated ammonium chloride and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (3×50 ml) and saturated brine solution (1×100 ml), dried (magnesium sulphate) and concentrated in vacuo to leave a crude orange oil. Flash chromatography (silica, 25% ethyl acetate in isohexane) gave 2.2 g of a pale yellow oil (67%).

후처리

  1. additionadded over 30 minutes
  2. customquenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined extracts were washed with water (3×50 ml) and saturated brine solution (1×100 ml)
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated in vacuo
  7. customto leave a crude orange oil

출처 및 근거

ORD 기록
ord-81cd7b7aae524d368ae7775492dbbe36
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887871B2

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