Hydrochloric Acid → HCID 15671501, compound

HRID 1088276Notes

Reaction equation

HRID 1088276 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[N+:12]([C:15]1[CH:39]=[CH:38][C:18]([CH2:19][O:20][C:21]([N:23]2[CH2:27][C@H:26]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:25][C@H:24]2[CH2:36]I)=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13].Cl>CN(C)C=O.O>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][C:21]([N:23]2[CH2:27][C@H:26]([O:28][Si:29]([C:32]([CH3:33])([CH3:35])[CH3:34])([CH3:30])[CH3:31])[CH2:25][C@H:24]2[CH2:36][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[O:22])=[CH:38][CH:39]=1)([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 15537960HCID 15537960, compound

Product 1

HCID 15671501HCID 15671501, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dimethyl malonate (660 mg) and 180 mg of 50% sodium hydride in 12.5 ml of dry dimethylformamide were stirred at room temperature in a nitrogen stream for 15 minutes, and 1.34 g of (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-iodomethyl-4-t-butyldimethylsilyloxypyrrolidine was added thereto. The resulting mixture was stirred at room temperature for 15 hours, neutralized with 3.75 ml of 1N hydrochloric acid, diluted with water, extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatogrphy to obtain (2R,4R)-1-(p-nitrobenzyloxycarbonyl)-2-(2,2-dimethoxycarbonylethyl)-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by silica gel chromatogrphy

Sources & evidence

ORD record
ord-b7921b94a7d94a10952b4a0e2d498d11
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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