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

반응식

HRID 2715 반응식
[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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6b6484c542a4422eb9a68c56a12b0a18
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731306

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