Sulfuric Acid → (2S, 4R)-4-methanesulfonyloxy-2-{5-(methylamino)-1,3,4-thiadiazol-2-yl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37259Notes

Reaction equation

HRID 37259 reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([C:24]([NH:26][NH:27][C:28]([NH:30][CH3:31])=O)=O)[CH2:7]1)(=[O:4])=[O:3].O.N.[S:34](=O)(=O)(O)O>>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([C:24]2[S:34][C:28]([NH:30][CH3:31])=[N:27][N:26]=2)[CH2:7]1)(=[O:4])=[O:3]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 12896473Azane;hydrateHCID 18638796(2S,4R)-4-methanesulfonyloxy-2-(4-methylsemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18638797(2S, 4R)-4-methanesulfonyloxy-2-{5-(methylamino)-1,3,4-thiadiazol-2-yl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Procedure

A suspension of (2S, 4R)-4-methanesulfonyloxy-2-(4-methylsemicarbazidocarbonyl)-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (2.00 g) in concentrated sulfuric acid (20 ml) was stirred at 0°-5° C. for 3 hours. The reaction mixture was poured into ice-water (200 ml), adjusted to pH 9 with concentrated ammonia water, extracted with dichloromethane (100 ml), 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 (1:99,V/V) to give (2S, 4R)-4-methanesulfonyloxy-2-{5-(methylamino)-1,3,4-thiadiazol-2-yl }-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.94 g).

Workup

  1. extractionextracted with dichloromethane (100 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a syrup
  5. washeluted with a mixture of methanol and chloroform (1:99,V/V)

Sources & evidence

ORD record
ord-3f4526be5e36475499862a3973eb6299
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

Loading…