Sulfuric Acid → HCID 53930560, compound

HRID 346352Notes

Reaction equation

HRID 346352 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][C:24]([OH:26])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:31][C:32]([NH2:34])=[O:33].S(=O)(=O)(O)O>C1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][C:24]([NH:31][C:32]([NH2:34])=[O:33])=[O:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1176UreaHCID 24386Thionyl ChlorideHCID 54131619HCID 54131619, compound

Product 1

HCID 53930560HCID 53930560, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-carboxymethyloxymethyl-4-methanesulfonyloxypyrrolidine (3.80 g) in benzene (19 ml) was added thionyl chloride (0.90 ml) with stirring at ambient temperature and the mixture was stirred at the same temperature for one hour. To the mixture were added urea (1.80 g) and concentrated sulfuric acid (0.05 ml) successively. The mixture was heated under reflux for 5 hours. The reaction mixture was poured into ice-water (100 ml) and extracted with ethyl acetate (100 ml). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (100 g) and eluted with a mixture of methanol and chloroform (1:99 V/V) to give (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[(ureidocarbonylmethyl)oxymethyl]pyrrolidine (1.85 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for one hour
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. extractionextracted with ethyl acetate (100 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluted with a mixture of methanol and chloroform (1:99 V/V)

Sources & evidence

ORD record
ord-6021552c932a4810a6190024a291eb94
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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