Phenyl isocyanate → Methyl 3-[2-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)ethyl]-4,5-dihydro-5-isoxazoleacetate

HRID 344826

반응식

HRID 344826 반응식
[C:1]([O:6][CH3:7])(=[O:5])[CH2:2][CH:3]=[CH2:4].C1(N=C=O)C=CC=CC=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=2[CH2:32][CH2:33][CH2:34][N+:35]([O-])=[O:36])=[CH:20][C:19]=1[CH3:38].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(N(CC)CC)C>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[C:25]=2[CH2:32][CH2:33][C:34]2[CH2:4][CH:3]([CH2:2][C:1]([O:6][CH3:7])=[O:5])[O:36][N:35]=2)=[CH:20][C:19]=1[CH3:38]

참가 물질

7

반응물 4

HCID 7672Phenyl isocyanate2회HCID 8471TriethylamineHCID 77314Methyl 3-butenoate2회HCID 540403614'-Fluoro-3,3',5-trimethyl-2-(3-nitropropyl)-1,1'-biphenyl

생성물 1

HCID 54381644Methyl 3-[2-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)ethyl]-4,5-dihydro-5-isoxazoleacetate수율 71.2%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 1140Toluene용매2회

실험 절차

A solution of 0.1 g (1.0 mmol) of methyl 3-butenoate and 0.174 ml (1.6 mmol) of phenyl isocyanate in 1 ml of toluene was added with stirring to a solution of 0.240 g (0.8 mmol) of the nitropropyl compound from Step D and 2 drops of triethylamine in 1 ml of toluene. The resulting mixture was stirred at room temperature for 3 hours. Additional quantities of methyl 3-butenoate (0.1 ml), triethylamine (0.1 ml) and phenyl isocyanate (0.15 ml) were added successively and stirring was continued overnight (18 hours). The mixture was filtered and the filtrate was concentrated in vacuo to a residue which was purified by flash chromatography on silica gel (230-400 mesh), first being eluted with methylene chloride to remove the impurities. Continued elution with acetone/methylene chloride (1:50, v/v) gave the desired product (0.218 g, 0.57 mmol, 71%) as a pale viscous oil. nmr (CDCl3) δ: 2.28 (6H, s), 2.32 (3H, s), 2.2-3.0 (6H, m), 3.70 (3H, s), 4.6-5.0 (H, m), 6.85 (H, bs), 7.0-7.2 (4H, m). IR (neat) 1735 cm-1

후처리

  1. stirringstirring
  2. waitwas continued overnight
  3. custom(18 hours)
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo to a residue which
  6. customwas purified by flash chromatography on silica gel (230-400 mesh)
  7. washfirst being eluted with methylene chloride
  8. customto remove the impurities
  9. washContinued elution with acetone/methylene chloride (1:50

출처 및 근거

ORD 기록
ord-aa311eec656c4fe7b866b87122ba700a
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05053525

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