Methyl iodide → Benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 247487노트

반응식

HRID 247487 반응식
[Cl:1][C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH:20]([N-]C(C)C)(C)C.[Li+].CI.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:20][CH:6]1[C:5](=[O:9])[N:4]2[CH:7]1[CH2:8][C:2]([Cl:1])=[C:3]2[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

참가 물질

7

반응물 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 12804728Benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2carboxylate

생성물 1

HCID 15136304Benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of benzyl 3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (56 mg) in anhydrous THF (0.5 ml) is added dropwise over a few minutes to a stirring solution of lithium diisopropylamide (from 31 μl diisopropylamine and 140 μl 1.6N BuLi) in anhydrous THF (3 ml) at -78°. After 15 more mins at -78°, the solution is treated with methyliodide (125 μl) and then allowed to warm to -20° over a period of 30 mins. Saturated aqueous NH4Cl (3 ml) is added and the mixture is allowed to come to room temperature. The mixture is diluted with EtOAc (50 ml), washed with pH 3 phosphate buffer, water, 5% NaHCO3, and brine, dried with magnesium sulfate, and evaporated in vacuo to give benzyl 6-methyl-3-chloro-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

후처리

  1. temperatureto warm to -20° over a period of 30 mins
  2. customto come to room temperature
  3. washwashed with pH 3 phosphate buffer, water, 5% NaHCO3, and brine
  4. dry with materialdried with magnesium sulfate
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-41d59d479c1740f88eae7f94a19e1e20
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04707547

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