Water → HCID 15671525, compound

HRID 1088284Notes

Reaction equation

HRID 1088284 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[N+:35]([C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1)([O-:37])=[O:36].O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][CH2:22][C:23]([O:25][CH2:42][C:41]2[CH:44]=[CH:45][C:38]([N+:35]([O-:37])=[O:36])=[CH:39][CH:40]=2)=[O:24])=[O:11])=[CH:26][CH:27]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 15671449HCID 15671449, compound

Product 1

HCID 15671525HCID 15671525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R,4S)-1-p-Nitrobenzyloxycarbonyl-2-(2-carboxyethyl)-4-acetylthiopyrrolidine (323 mg) was dissolved in 3.3 ml of dry dimethylformamide, and 150 mg of triethylamine and 324 mg of p-nitrobenzyl bromide were added thereto, followed by stirring at room temperature for 3.5 hours. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate, washed successively with a saturated sodium bicarbonate solution, water, dilute hydrochloric acid and water, dried over anhydrous sodium sulfate and distilled off to remove the solvent. The residue was purified by silica gel column chromatography to obtain (2R,4S)-1-p-nitrobenzyloxycarbonyl-2-(2-p-nitrobenzyloxycarbonylethyl)-4-acetylthiopyrrolidine.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washwashed successively with a saturated sodium bicarbonate solution, water, dilute hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled off
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fd6c96da62bb4f81a38ab382b07824e2
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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