Isoindoline → HCID 68227310, compound

HRID 1400132Notes

Reaction equation

HRID 1400132 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]([C:15]1([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:22](=[O:34])[C:21]3=[O:35])[CH2:17][CH2:16]1)=[O:14])[CH3:11]>O1CCCC1>[C:30]([O:29][C:27]([NH:23][C:24]1[CH:25]=[CH:26][C:18]([C:15]2([C:13]([O:12][CH2:10][CH3:11])=[O:14])[CH2:16][CH2:17]2)=[CH:19][C:20]=1[C:21](=[O:35])[C:22]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:34])=[O:28])([CH3:32])([CH3:31])[CH3:33]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 67154027HCID 67154027, compound

Product 1

HCID 68227310HCID 68227310, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

3.2 g of isoindoline are added to 9.3 g of 5-(1-ethoxycarbonylcyclopropyl)-1-tert-butoxycarbonyl-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 4.0 g (32%) of ethyl 1-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]cyclopropanecarboxylate;

Workup

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

Sources & evidence

ORD record
ord-55b93eb8ea9242538296ff3caea16a37
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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