Ammonium Chloride → {1-Cyano-3-ethyl-5-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-pent-3-enyl}-phosphonic Acid Diethyl Ester

HRID 33657

반응식

HRID 33657 반응식
[C:1]([CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:23][C:24]([CH2:47][CH3:48])=[CH:25][CH2:26][C:27]1[C:35]([O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])=[C:34]2[C:30]([CH2:31][O:32][C:33]2=[O:43])=[C:29]([CH3:44])[C:28]=1[O:45][CH3:46].[Cl-].[NH4+]>C1COCC1>[CH2:6]([O:5][P:4]([CH:3]([C:1]#[N:2])[CH2:23][C:24]([CH2:47][CH3:48])=[CH:25][CH2:26][C:27]1[C:35]([O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:40])[CH3:41])=[C:34]2[C:30](=[C:29]([CH3:44])[C:28]=1[O:45][CH3:46])[CH2:31][O:32][C:33]2=[O:43])(=[O:11])[O:8][CH2:9][CH3:10])[CH3:7]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 670098846-(3-Bromomethyl-pent-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

생성물 1

HCID 72563633{1-Cyano-3-ethyl-5-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-pent-3-enyl}-phosphonic Acid Diethyl Ester수율 42%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of diethyl cyanomethylphosphonate (233 mg, 1.32 mmol) in THF (1 mL) was added a THF solution of sodium bis(trimethysilyl)amide (1.0 M, 1.21 mL, 1.21 mmol). After stirring for 30 minutes, the solution was added dropwise to a solution of 6-(3-bromomethyl-pent-2-enyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (100 mg, 0.22 mmol) in THF (1 mL). The resulting mixture was allowed to stir at room temperature overnight before saturated aqueous ammonium chloride was added. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to dryness. The residue was purified by preparative reverse-phase HPLC, affording 51 mg (42%) of the desired product.

후처리

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-ca22cd4441b14d3193294ff1556e1eec
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429565B2

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