Isoindoline → HCID 67154010, compound

HRID 1400145Notes

Reaction equation

HRID 1400145 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:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:25](=[O:37])[C:24]2=[O:38])[CH2:16][CH2:17][CH:18]([F:20])[F:19])=[O:14])[CH3:11]>O1CCCC1>[C:33]([O:32][C:30]([NH:26][C:27]1[CH:28]=[CH:29][C:21]([CH:15]([CH2:16][CH2:17][CH:18]([F:19])[F:20])[C:13]([O:12][CH2:10][CH3:11])=[O:14])=[CH:22][C:23]=1[C:24](=[O:38])[C:25]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:37])=[O:31])([CH3:35])([CH3:34])[CH3:36]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 67154018HCID 67154018, compound

Product 1

HCID 67154010HCID 67154010, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

1.53 g of isoindoline are added to 5.29 g of 5-(1-ethoxycarbonyl-4,4-difluorobutyl)-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 1.7 g (25%) of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]-5,5-difluoropentanoate; LC-MS retention time: 2.62 min (“nonpolar” gradient).

Workup

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

Sources & evidence

ORD record
ord-f538251f79594564bc88f39003bb5f98
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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