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 1418019Notes

Reaction equation

HRID 1418019 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6c5605bbfe594116971270018d17f8a5
Source dataset
uspto-grants-1999_03
Patent number
US05880119

Reaction notes

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