Isoindoline → HCID 67154051, compound

HRID 1400155Notes

Reaction equation

HRID 1400155 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:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:24](=[O:36])[C:23]2=[O:37])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[CH3:11]>O1CCCC1>[C:32]([O:31][C:29]([NH:25][C:26]1[CH:27]=[CH:28][C:20]([CH:15]([CH2:16][CH2:17][CH2:18][CH3:19])[C:13]([O:12][CH2:10][CH3:11])=[O:14])=[CH:21][C:22]=1[C:23](=[O:37])[C:24]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:36])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 67154049HCID 67154049, compound

Product 1

HCID 67154051HCID 67154051, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

1.95 g of isoindoline are added to 6.4 g of 5-(1-ethoxycarbonylpentyl)-1-tertbutoxycarbonyl-2,3-dioxoindoline in 100 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 3.8 g (46%) of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]hexanoate; LC-MS retention time: 2.89 min (“nonpolar” gradient).

Workup

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

Sources & evidence

ORD record
ord-eb4034fea70640a9acdfe333361478d3
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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