Toluene → HCID 90251321, compound

HRID 2275789Notes

Reaction equation

HRID 2275789 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])[CH2:10]C(O)=O.C([N:27]([CH2:30]C)CC)C.C1(C)C=CC=CC=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])C=CC=CC=1.[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57]>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24])[CH2:10][NH:27][C:30](=[O:46])[O:60][C:56]([CH3:59])([CH3:58])[CH3:57]

Participants

7

Reactant 5

HCID 1140TolueneHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 90114262HCID 90114262, compound

Product 1

HCID 90251321HCID 90251321, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon, 2.17 g of rac-3-(2,4-difluorophenyl)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-propanoic acid (Example 49A, 6.54 mmol) and 1.32 g of triethylamine (13.07 mmol) were initially charged in 23.8 ml of abs. toluene. 1.89 g of diphenylphosphoryl azide (6.86 mmol) were added at RT, and the mixture was stirred at RT with water cooling for 3.5 h, 23.8 ml of tert-butanol were then added and the mixture was stirred under reflux overnight. After cooling, the reaction solution was concentrated and purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 2:1). This gave 650 mg of the title compound (24% of theory).

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. concentrationthe reaction solution was concentrated
  4. custompurified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-dd3de46323de423c806393fb65c3bbe7
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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