Hydrochloric Acid → HCID 15086211, compound

HRID 1088628Notes

Reaction equation

HRID 1088628 reaction equation
Cl.[Si]([O:9][C@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[C@H:12]([CH2:28][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH2:11]1)(C(C)(C)C)(C)C.C(=O)([O-])O.[Na+].C(Cl)(Cl)Cl>CO.O>[OH:9][C@H:10]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:12]([CH2:28][N:29]2[CH:33]=[CH:32][N:31]=[CH:30]2)[CH2:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 15086209HCID 15086209, compound

Product 1

HCID 15086211HCID 15086211, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Conc. hydrochloric acid (0.5 ml) was added to a solution of (2S,4R)-4-t-butyldimethylsilyloxy-2-(imidazol-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine (1.55 g) in methanol (15 ml). After stirring at ambient temperature for one hour, saturated aqueous sodium hydrogen carbonate (3 ml) was added to the mixture. The reaction mixture was concentrated under reduced pressure to give a residue. To the residue was added a mixture of chloroform (30 ml) and water (30 ml). The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (2:98, V/V) to give (2S,4R)-4-hydroxy-2-(imidazol-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (0.80 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue
  3. additionTo the residue was added
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluted with a mixture of methanol and chloroform (2:98, V/V)

Sources & evidence

ORD record
ord-e014b1d77c2b4d6588d6f87e54c9d6ce
Source dataset
uspto-grants-1990_10
Patent number
US04963544

Reaction notes

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