4-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamide → N-(4-Benzoylbenzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide

HRID 1889673노트

반응식

HRID 1889673 반응식
[Cl:1][C:2]1[C:3]([OH:34])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[CH:33]=[CH:32][C:25]([C:26](N(OC)C)=[O:27])=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:35]1([Mg]Br)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[C:26]([C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[S:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[OH:34])(=[O:11])=[O:10])=[CH:33][CH:32]=1)(=[O:27])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

4

반응물 2

HCID 585315364-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamideHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 58531392N-(4-Benzoylbenzyl)-3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxybenzenesulfonamide수율 42.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamide (0.105 g, 0.20 mmol) in THF (2 mL) was added phenylmagnesium bromide (3M in ether, 0.267 mL, 0.800 mmol). The resulting mixture was stirred at rt overnight. The mixture was quenched by adding cold saturated aq. NH4Ac solution and extracted with DCM. The combined organic extracts were dried and concentrated. The residue was purified by preparative HPLC. The desired fractions were combined, concentrated and lyophilized to dryness to give the title compound (46 mg, 42%) as a tan solid. MS (ESI): 544.1 (M+H)+.

후처리

  1. customThe mixture was quenched
  2. additionby adding cold saturated aq. NH4Ac solution
  3. extractionextracted with DCM
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8669bf85891f4e3eab51f9462b7982fa
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501992B2

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