Tetrahydrofuran → HCID 15086213, compound

HRID 1613988Notes

Reaction equation

HRID 1613988 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[O:13])[C@H:9]([CH2:25][N:26]2[CH:30]=[CH:29][N:28]=[CH:27]2)[CH2:8]1.O1CCCC1>C(N(CC)CC)C.ClCCl.O>[N:26]1([CH2:25][C@@H:9]2[CH2:8][C@@H:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:11][N:10]2[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[O:13])[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 15086211HCID 15086211, compound

Product 1

HCID 15086213HCID 15086213, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
2.5 °C

Procedure

Methanesulfonyl chloride (0.40 ml) was added to a suspension of (2S,4R)-4-hydroxy-2-(imidazol-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.79g) in a mixture of triethylamine (0.80 ml), tetrahydrofuran (16 ml) and dichloromethane (24 ml) at 0-5° C., and the mixture was stirred at 0-5° C. for one hour. The reaction mixture was poured into a mixture of water (50 ml) and dichloromethane (20 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)-2-(imidazol-1-yl)methyl-4-methanesulfonyloxy1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.78 g).

Workup

  1. customThe organic layer was separated
  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 (2:98, V/V)

Sources & evidence

ORD record
ord-4f48fbc1b2ff4845808a93e32522e3e0
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

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