Isoindoline → HCID 67154074, compound

HRID 1400150Notes

Reaction equation

HRID 1400150 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]([CH:15]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:23](=[O:35])[C:22]2=[O:36])[CH2:16][CH2:17][CH3:18])=[O:14])[CH3:11]>O1CCCC1>[C:31]([O:30][C:28]([NH:24][C:25]1[CH:26]=[CH:27][C:19]([CH:15]([CH2:16][CH2:17][CH3:18])[C:13]([O:12][CH2:10][CH3:11])=[O:14])=[CH:20][C:21]=1[C:22](=[O:36])[C:23]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:35])=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 67154036HCID 67154036, compound

Product 1

HCID 67154074HCID 67154074, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

1.12 g of isoindoline are added to 3.5 g of 5-(1-ethoxycarbonylbutyl)-1-tertbutoxycarbonyl-2,3-dioxoindoline in 50 ml of tetrahydrofuran, and the mixture is subsequently stirred at 23° C. for 1 h. The mixture is evaporated to dryness in vacuo and purified by column chromatography, giving 1.4 g (30%) of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]-pentanoate; LC-MS retention time: 2.78 min (“nonpolar” gradient).

Workup

  1. customThe mixture is evaporated to dryness in vacuo
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-6ffebab614124e56a44b8e2b75baab16
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

Loading…