Isoindoline → HCID 68227475, compound

HRID 1400121Notes

Reaction equation

HRID 1400121 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[CH2:10]([O:12][C:13](=[O:33])[CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19](=[O:31])[C:18]2=[O:32])[CH3:11]>O1CCCC1>[C:27]([O:26][C:24]([NH:20][C:21]1[CH:22]=[CH:23][C:15]([CH2:14][C:13]([O:12][CH2:10][CH3:11])=[O:33])=[CH:16][C:17]=1[C:18](=[O:32])[C:19]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:31])=[O:25])([CH3:29])([CH3:28])[CH3:30]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 68227316HCID 68227316, compound

Product 1

HCID 68227475HCID 68227475, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

2.2 g of isoindoline are added to 5.9 g of tert-butyl 5-(2-ethoxy-2-oxoethyl)-2,3-dioxoindoline-1-carboxylate in 100 ml of tetrahydrofuran, and the mixture is subsequently stirred at 23° C. for 1 h. The solvent is removed in vacuo, and the residue is purified by column chromatography, giving 4.9 g of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]acetate;

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-b89296b670e64a9db1941dfd3d54c616
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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