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Ammonium Acetate → Isopropyl 4-[1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate

HRID 1371026
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HRID 1371026 반응식
[CH:1]([O:4][C:5](=[O:22])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:14])=[CH:8][CH:7]=1)([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([P:40](=[O:51])([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])([F:39])[F:38])=[CH:33][CH:32]=1.C([O-])(=O)C.[NH4+]>C1COCC1>[C:47]([O:46][P:40]([C:37]([F:39])([F:38])[C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:22])=[CH:7][CH:8]=2)[C:13]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[O:14])=[CH:32][CH:33]=1)([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:51])([CH3:48])([CH3:49])[CH3:50]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 517165Ammonium AcetateHCID 15922636Di(tert-butyl) [4-(bromomethyl)phenyl](difluoro)methylphosphonateHCID 18510263Isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 18510274Isopropyl 4-[1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate (0.130 g, 0.433 mmol), (Example 4, Step 1) 18-crown-6 (0.03 g) in THF (2.2 ml ) at −2020 C. was added a solution of potassium tert-butoxide 1 M in THF (0.475 ml). To the reaction mixture was added a solution of di(tert-butyl) [4-(bromomethyl)phenyl](difluoro)methylphosphonate (0.196 g, 0.475 mmol) in THF (5 ml). The reaction was stirred at room temperature for 1 hour, and then saturated ammonium acetate solution (20 ml) was added and the mixture was extracted with ethyl acetate (20 ml). The organic phase was washed with brine, dried over sodium sulfate, filtered, and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 15% plus 1% triethylamine giving 0.05 g of the title compound.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (20 ml)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-311973521cb841a19e31eef3ae7333c2
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06583126B2

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