Sodium Thiosulfate → HCID 69675660, compound

HRID 1751678Notes

Reaction equation

HRID 1751678 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-c2ae556dbbee4fb08831e9a341ac77bf
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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