Diisopropylamine → N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-hydroxypropyl)-azetidin-2-one

HRID 247481

반응식

HRID 247481 반응식
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH3:14].[Si:24]([N:31]1[CH:34]([CH2:35][CH:36]=[O:37])[CH2:33][C:32]1=[O:38])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CCCCCC.C1COCC1>[Si:24]([N:31]1[CH:34]([CH2:35][CH:36]([OH:37])[CH2:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:33][C:32]1=[O:38])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 8785Benzyl acetateHCID 128047181-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinoneHCID 178418339Butyllithium

생성물 1

HCID 12804719N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-hydroxypropyl)-azetidin-2-one수율 96.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a flame dried, 50 ml, 3-neck flask fitted with a N2 inlet, magnetic stirrer, addition funnel, and serum cap are added anhydrous tetrahydrofuran(THF) (10.5 ml) and diisopropyl amine (0.579 ml, 4.13 mmol). The solution is cooled in an ice-methanol bath under N2 and treated with 2.4N n-butyl lithium in hexane (1.72 ml). After being stirred at -10° for 15 mins, the solution is cooled to -78° and treated dropwise over 9 mins with a solution of benzyl acetate (0.620 g, 4.13 mmol) in anhydrous THF (3.5 ml). After stirring for 15 more mins at -78° C. the reaction mixture is treated dropwise over 13 mins with a solution of N-(t-butyldimethylsilyl)-4-(2-oxoethyl)-azetidin-2-one (0.894 g, 3.93 mmol) in anhydrous THF (6 ml). The reaction mixture is stirred at -78° an additional 15 mins and then quenched with 2.5N HCl (6 ml). EtOAc (100 ml) is added and the organic phase is separated, washed with H2O (2×20 ml), 5% NaHCO3 (20 ml) and brine, dried with MgSO4, and filtered. The filtrate is evaporated i.v. and the residue stripped with φH to yield N-(t-butyldimethylsilyl)-4-(3-benzyloxycarbonyl-2-hydroxypropyl)-azetidin-2-one (1.432 g) as on oil: ir(neat) 2.87, 5.73, 5.79. 7.57, 7.96, 8.39, 11.92, and 12.16 cm-1 ; mass spectrum m/e 362, 320, 278, 170 and 128.

후처리

  1. customTo a flame dried
  2. custom50 ml, 3-neck flask fitted with a N2 inlet, magnetic stirrer, addition funnel
  3. customserum cap
  4. temperatureThe solution is cooled in an ice-methanol bath under N2
  5. temperaturethe solution is cooled to -78°
  6. stirringAfter stirring for 15 more mins at -78° C. the reaction mixture
  7. stirringThe reaction mixture is stirred at -78° an additional 15 mins
  8. customquenched with 2.5N HCl (6 ml)
  9. additionEtOAc (100 ml) is added
  10. customthe organic phase is separated
  11. washwashed with H2O (2×20 ml), 5% NaHCO3 (20 ml) and brine
  12. dry with materialdried with MgSO4
  13. filtrationfiltered
  14. customThe filtrate is evaporated i.v

출처 및 근거

ORD 기록
ord-c0fd08612b114dccae0905a3a35e18cb
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04707547

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