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 1889673ノート

反応式

HRID 1889673 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-8669bf85891f4e3eab51f9462b7982fa
出典データセット
uspto-grants-2013_08
特許番号
US08501992B2

反応ノート

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