Sodium Thiosulfate → HCID 69675660, compound

HRID 1509700Notes

Reaction equation

HRID 1509700 reaction equation
[I:1][C:2]1[N:3]=[C:4]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([CH3:13])[N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[NH:5][C:6]=1I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[I:1][C:2]1[NH:3][C:4]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([CH3:13])[N:9]2[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 24477Sodium ThiosulfateHCID 69675653HCID 69675653, compound

Product 1

HCID 69675660HCID 69675660, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (2S,5S)-tert-butyl 2-(4,5-diiodo-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate (4.28 g, 8.50 mmol) in ethanol (75 mL) and water (75 mL), sodium thiosulfate (10.72 g, 85.1 mmol) was added and the reaction mixture was stirred vigorously for 1 hour at 100° C., 16 hours at 90° C., and 5 hours at 100° C. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was washed additionally with ethyl acetate and the organic layers were combined. The organic layer was dried with sodium sulfate, concentrated and the crude material was purified by column chromatography to yield (2S,5S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate as a white solid (2.34 g, 6.20 mmol, 73%). 1H NMR (400 MHz, cdcl3) δ 7.04 (s, 1H), 4.89 (dd, 1H), 3.92 (m, 1H), 2.91 (s, 1H), 2.18-2.06 (m, 2H), 1.78 (m, 1H), 1.52 (m, 1H), 1.48 (s, 9H), 1.13 (d, 3H).

Workup

  1. custom5 hours
  2. customat 100° C
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe aqueous layer was washed additionally with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated
  7. customthe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-8f552e14a87e4f9b97f889b294ab9992
Source dataset
uspto-grants-2015_12
Patent number
US09221833B2

Reaction notes

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