Lithium iodide → HCID 54224375, compound

HRID 611744Notes

Reaction equation

HRID 611744 reaction equation
C[O:2][C:3](=[O:41])[C@H:4]([O:18][C:19]1[C:24]([Br:25])=[CH:23][C:22]([C:26]2[C:34]3[C:33]4[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=4[S:31][C:30]=3[CH:29]=[CH:28][C:27]=2[Br:39])=[CH:21][C:20]=1[Br:40])[CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[I-].[Li+]>N1C=CC=CC=1>[Br:25][C:24]1[CH:23]=[C:22]([C:26]2[C:34]3[C:33]4[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=4[S:31][C:30]=3[CH:29]=[CH:28][C:27]=2[Br:39])[CH:21]=[C:20]([Br:40])[C:19]=1[O:18][C@H:4]([CH2:5][CH2:6][N:7]1[C:8](=[O:17])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:15]1=[O:16])[C:3]([OH:41])=[O:2]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 54451052HCID 54451052, compound

Product 1

HCID 54224375HCID 54224375, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (R)-2-[2,6-dibromo-4-(2-bromo-dibenzothiophen-1-yl)-phenoxy]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester (0.514 g, 0.68 mmol) and lithium iodide (0.915 g, 6.8 mmol) in pyridine (20 mL) was stirred at 110° C. After 2 days, the mixture was quenched with 10% aqueous HCl and further diluted with water (150 mL). Aqueous mixture was extracted with dichloromethane (150 mL). The dichloromethane extract was washed with water, dried with brine. Silica gel was added. Solvent was removed and the adsorbate was flash chromatographed (eluent 7:3 petroleum ether:ethyl acetate) to provide the title compound as a white solid (0.319 g, 63%): mp 130-132° C.: NMR (CDCl3): δ 7.86 (dd, J=8, 1 Hz, 2H), 7.81 (d, J=8 Hz, 1H), 7.77-7.70 (m, 4 H), 7.52 (d, J=1 Hz, 2H), 7.39 (ddd, J=8, 7, 1 Hz, 1H), 7.18 (ddd, J=8, 7, 1 Hz, 1H), 6.77 (d, J=8 Hz, 1H), 5.24 (t, J=7 Hz, 1H), 4.21-4.05 (m, 2 H), 2.67-2.55 (m, 2H); MS (+EI): [M+], 3 bromine isotope pattern, 741, 743, 745, 747; Anal. Calc. for C3OH18Br3NO5S: C 48.86, H, 2.74, N, 1.83. Found: C 48.90, H, 2.82, N, 1.18.

Workup

  1. customthe mixture was quenched with 10% aqueous HCl
  2. additionfurther diluted with water (150 mL)
  3. extractionAqueous mixture was extracted with dichloromethane (150 mL)
  4. extractionThe dichloromethane extract
  5. washwas washed with water
  6. dry with materialdried with brine
  7. additionSilica gel was added
  8. customSolvent was removed
  9. customchromatographed (eluent 7:3 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-14cb6a8feb2a4c3fa354972a589fe633
Source dataset
uspto-grants-1999_12
Patent number
US06001867

Reaction notes

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