tert-Butanol → HCID 90132492, compound

HRID 2275788Notes

Reaction equation

HRID 2275788 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:10]C(O)=O)[CH:5]=[CH:6][C:7]=1[F:8].C([N:27]([CH2:30]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.[C:49]([OH:53])([CH3:52])([CH3:51])[CH3:50]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:10][NH:27][C:30](=[O:39])[O:53][C:49]([CH3:52])([CH3:51])[CH3:50])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 90113879HCID 90113879, compound

Product 1

HCID 90132492HCID 90132492, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under argon, a solution of 5.0 g of rac-3-(3,4-difluorophenyl)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoic acid (Example 48A, 15.09 mmol) and 3.06 g of triethylamine (30.19 mmol) in 65 ml of toluene was initially charged, 4.36 g of diphenylphosphoryl azide (15.85 mmol) were added and the mixture was stirred at RT for 3.5 h. 65 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: petroleum ether/ethyl acetate 2:1, isocratic). This gave 3.1 g of the title compound (45% of theory).

Workup

  1. stirringthe mixture was stirred
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe reaction solution was concentrated
  5. custompurified by flash chromatography (mobile phase: petroleum ether/ethyl acetate 2:1, isocratic)

Sources & evidence

ORD record
ord-f2034e8ba0c4425497eddf022706986e
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…