Isoindoline → HCID 67154064, compound

HRID 1400160Notes

Reaction equation

HRID 1400160 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.[F:10][CH:11]([F:43])[CH2:12][CH2:13][C:14]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:29](=[O:41])[C:28]2=[O:42])([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:15][CH2:16][CH:17]([F:19])[F:18]>O1CCCC1>[C:37]([O:36][C:34]([NH:30][C:31]1[CH:32]=[CH:33][C:25]([C:14]([CH2:15][CH2:16][CH:17]([F:19])[F:18])([CH2:13][CH2:12][CH:11]([F:43])[F:10])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:26][C:27]=1[C:28](=[O:42])[C:29]([N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:41])=[O:35])([CH3:39])([CH3:38])[CH3:40]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 67154038HCID 67154038, compound

Product 1

HCID 67154064HCID 67154064, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

584 mg of isoindoline are added to 2.4 g of 5-[1-(3,3-difluoropropyl)-1-ethoxycarbonyl-4,4-difluorobutyl]-1-tert-butoxycarbonyl-2,3-dioxoindoline in 30 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 700 mg (24%) of ethyl 2-[4-(tert-butoxycarbonylamino)-3-(2-isoindolin-2-yl-2-oxoacetyl)phenyl]-2-(3,3-difluoropropyl)-5,5-difluoropentanoate;

Workup

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

Sources & evidence

ORD record
ord-2c9398d2eb0a4588adbd7764753f1b90
Source dataset
uspto-grants-2014_12
Patent number
US08906930B2

Reaction notes

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