Ethyl Acetate → {4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl Ester

HRID 272212

반응식

HRID 272212 반응식
[C:1]1([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]2[C:22]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[C:23]3[C:27](=[C:28]([CH3:32])[C:29]=2[O:30][CH3:31])[CH2:26][O:25][C:24]3=[O:33])(=[O:16])[O:9]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CCOC(C)=O>C1COCC1>[C:1]1([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]2[C:22]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:38])[CH3:39])=[C:23]3[C:27](=[C:28]([CH3:32])[C:29]=2[O:30][CH3:31])[CH2:26][O:25][C:24]3=[O:33])(=[O:9])[OH:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 76546201{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Diphenyl Ester

생성물 1

HCID 76548829{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl Ester수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of {4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic acid diphenyl ester (75 mg, 0.126 mmol) in THF (5 mL) was added 1N NaOH (0.1 mL) solution. The mixture was allowed to stir at room temperature for 16 hours. EtOAc was added and the resulting mixture was washed with 1H HCl. The organic layer was concentrated to dryness and the residue was purified by RP HPLC using a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, 0.1% TFA to provide 24.8 mg (38%) of the desired product. MS (m/z) 517 [M−H]−, 541 [M+Na]+.

후처리

  1. washthe resulting mixture was washed with 1H HCl
  2. concentrationThe organic layer was concentrated to dryness
  3. customthe residue was purified by RP HPLC

출처 및 근거

ORD 기록
ord-04475c27979643b5863a5d5da1a233e0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452901B2

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