Sodium Bicarbonate → HCID 59668868, compound

HRID 588959Notes

Reaction equation

HRID 588959 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][C@@H:16](O)[CH2:15][N:14]3[C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.COCCN(S(F)(F)[F:39])CCOC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][C@H:16]([F:39])[CH2:15][N:14]3[C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 59668698(2S,4R)-benzyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 59668868HCID 59668868, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(2S,4R)-benzyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (1.5 g, 3.4 mmol) was added as a solid to a solution of bis(2-methoxyethyl)aminosulfur trifluoride (0.98 mL, 5.1 mmol) in 15 mL CH2Cl2 cooled to −78° C. Reaction was stirred at −78° C. for two hours and then warmed to room temperature and stirred for 2 hours. Reaction was poured into saturated sodium bicarbonate solution and stirred until bubbling ceased. Layers were separated and aqueous layer washed one time with CH2Cl2. Combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to give a yellow oil. The oil was triturated with CH2Cl2 and pentane to yield (2S,4S)-benzyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-fluoropyrrolidine-1-carboxylate JG-20 as a yellow solid (0.96 g, 62%).

Workup

  1. customReaction
  2. temperaturewarmed to room temperature
  3. stirringstirred for 2 hours
  4. customReaction
  5. stirringstirred
  6. customuntil bubbling
  7. customLayers were separated
  8. washaqueous layer washed one time with CH2Cl2
  9. washCombined organics were washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give a yellow oil
  14. customThe oil was triturated with CH2Cl2 and pentane

Sources & evidence

ORD record
ord-dcfa394a20074492871aa464b97a6f47
Source dataset
uspto-grants-2016_01
Patent number
US09227961B2

Reaction notes

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