3-Chloro-2,2-dimethylpropanoyl chloride → p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoate

HRID 2371895노트

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HRID 2371895 반응식
C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+].[C:13]([S:17][CH:18]1[N:21]([CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:20](=[O:36])[CH2:19]1)([CH3:16])([CH3:15])[CH3:14].[Cl:37][CH2:38][C:39]([CH3:44])([CH3:43])[C:40](Cl)=[O:41]>C1COCC1.C1(C)C=CC=CC=1.Cl.[Na+].[Cl-]>[C:13]([S:17][CH:18]1[N:21]([CH:22]([C:40](=[O:41])[C:39]([CH3:44])([CH3:43])[CH2:38][Cl:37])[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)=[O:24])[C:20](=[O:36])[CH2:19]1)([CH3:16])([CH3:14])[CH3:15]

참가 물질

8

반응물 3

HCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 14460289p-Nitrobenzyl (4-tert-butylthio-2-oxo-1-azetidinyl)acetateHCID 86588160Lithim bis(trimethylsilylamide)

생성물 1

HCID 14460305p-Nitrobenzyl 2-(4-tert-butylthio-2-oxo-1-azetidinyl)-5-chloro-4,4-dimethyl-3-oxopentanoate수율 69.4%

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 1140Toluene용매HCID 5234Sodium Chloride용매HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

6 ml of a 1M solution of lithium bis(trimethylsilylamide) in THF is slowly added dropwise to a stirred mixture, at 70° C., of 1.06 g (3 mmol) of p-nitrobenzyl 2-(4-tertbutylthio-2-oxo-1-azetidinyl)acetate and 410 μl (3.17 mmol) of chloropivaloyl chloride in 38 ml of absolute tetrahydrofuran, and the mixture is stirred for a further 30 minutes at -70° C. The reaction mixture is diluted with 250 ml of toluene, and 10 ml of 2N aqueous HCl and 100 ml of saturated NaCl solution are added. After separation, the organic phase is again washed with 100 ml of saturated NaCl solution then dried over MgSO4, and filtered, and the solvent is removed in vacuo on a rotary evaporator. The non-crystalline residue is chromatographed over 46 g of silica gel using toluene:ethyl acetate (19:1), to give 980 mg of non-crystalline title compound. IR in CH2Cl2 : 2930, 1770, 1760, 1725, 1615, 1530, 1465, 1370, 1250, 1215, 1190, 1110, 1040, 1000, 847 cm-1.

후처리

  1. additionare added
  2. customAfter separation
  3. washthe organic phase is again washed with 100 ml of saturated NaCl solution
  4. dry with materialthen dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo on a rotary evaporator
  7. customThe non-crystalline residue is chromatographed over 46 g of silica gel

출처 및 근거

ORD 기록
ord-279b1b53757941a48299cb50d5acb403
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05096899

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