Trifluoroacetic acid → 4-Hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21094노트

반응식

HRID 21094 반응식
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH:7](O)[N:8]([C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:9]2=[O:15].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[OH:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH2:7][N:8]([C:16]([CH3:24])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:17])[C:9]2=[O:15].[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([I:14])=[C:10]2[C:6]=1[CH2:7][N:8]([C:16]([CH3:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])[C:9]2=[O:15]

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684919774-Methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

생성물 2

HCID 684893914-Hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone수율 59%HCID 68490938HCID 68490938, 화합물수율 27%

시약·촉매·용매 1

HCID 6375Nitromethane용매

실험 절차

In a similar manner to Step 4 of Example 16, 4-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (500 mg, 1.10 mmol) was dissolved in nitromethane (25 mL), and the solution was treated with trifluoroacetic acid (0.525 mL, 6.82 mmol) and triethylsilane (0.527 mL, 3.30 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/0, 99/1) to obtain 4-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (257 mg, yield 59%) and 4-methoxymethoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (131 mg, yield 27%).

후처리

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=100/0, 99/1)

출처 및 근거

ORD 기록
ord-d928066073f843f3bedb7368cd7aa256
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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