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

HRID 371280노트

반응식

HRID 371280 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-fa0a129754d64ccd8b58d4106b86fe1f
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04530841

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