Isoindoline → HCID 68227402, compound

HRID 1400138Notes

Reaction equation

HRID 1400138 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:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:23](=[O:35])[C:22]3=[O:36])[CH2:18][CH2:17][CH2:16]1)=[O:14])[CH3:11]>O1CCCC1>[C:31]([O:30][C:28]([NH:24][C:25]1[CH:26]=[CH:27][C:19]([C:15]2([C:13]([O:12][CH2:10][CH3:11])=[O:14])[CH2:16][CH2:17][CH2:18]2)=[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])([CH3:33])([CH3:32])[CH3:34]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 67154054HCID 67154054, compound

Product 1

HCID 68227402HCID 68227402, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

1.049 g of isoindoline are added to 3.3 g of 5-(1-ethoxycarbonylcyclobutyl)-1-tert-butoxycarbonyl-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 1.2 g (28%) of ethyl 1-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]cyclobutanecarboxylate; LC-MS retention time: 2.75 min (“nonpolar” gradient).

Workup

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

Sources & evidence

ORD record
ord-165714afc7824f11b543d731226401aa
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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