Tetrabutylammonium Fluoride → 2-{2-[2-Carboxy-2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester

HRID 2715

反応式

HRID 2715 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:34]([O:36]CC[Si](C)(C)C)=[O:35])[CH2:13][C:14]1[CH:33]=[CH:32][CH:31]=[CH:30][C:15]=1[CH2:16][NH:17][CH:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:34]([CH:12]([N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1])[CH2:13][C:14]1[CH:33]=[CH:32][CH:31]=[CH:30][C:15]=1[CH2:16][NH:17][CH:18]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])([OH:36])=[O:35]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317205832-{2-[2-(1,3-Dioxo-1,3,dihydro-isoindol-2-yl)-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester

生成物 1

HCID 1317205842-{2-[2-Carboxy-2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester収率 102.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Dissolve 2-{2-[2-(1,3-dioxo-1,3,dihydro-isoindol-2-yl)-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-benzylamino}-4-methyl-valeric acid, tert-butyl ester (221 mg, 0.372 mmol) in tetrahydrofuran (5 mL) and treat with tetrabutylammonium fluoride (0.43 mL of a 1.0M solution in tetrahydrofuran, 0.43 mmol). Stir for 1.5 hours, evaporate the solvent in vacuo and dissolve the residue in ethyl acetate (75 mL). Wash with 1N hydrochloric acid (25 mL) and brine (25 mL). Dry (Na2SO4) and evaporate the solvent in vacuo to give the title compound as a white solid (188 mg).

後処理

  1. customevaporate the solvent in vacuo
  2. dissolutiondissolve the residue in ethyl acetate (75 mL)
  3. washWash with 1N hydrochloric acid (25 mL) and brine (25 mL)
  4. dry with materialDry (Na2SO4)
  5. customevaporate the solvent in vacuo

出典と根拠

ORDレコード
ord-6b6484c542a4422eb9a68c56a12b0a18
出典データセット
uspto-grants-1998_03
特許番号
US05731306

関連ノート

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