Water → HCID 54062624, compound

HRID 975650Notes

Reaction equation

HRID 975650 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[CH:17]=[CH:18][C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>C(OCC)(=O)C.CN(C)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:13][C@H:12]1[CH:17]=[CH:18][C:19]1[N:20]([CH3:24])[CH:21]=[CH:22][N:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 54305707HCID 54305707, compound

Product 1

HCID 54062624HCID 54062624, compound

Reagents, catalysts & solvents 2

HCID 1146TrimethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-4-hydroxy-2-[2-(1-methylimidazol-2-yl)vinyl]pyrrolidine (5.45 g) in a mixture of ethyl acetate (60 ml) and trimethylamine (3.01 ml) was added dropwise methanesulfonyl chloride (1.42 ml) under ice-cooling with stirring and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added ethyl acetate (100 ml) and water (50 ml). The organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of dichloromethane and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[2-(1-methylimidazol-2-yl)vinyl]pyrrolidine (5.70 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was chromatographed on silica gel (150 g)
  7. washeluting with a mixture of dichloromethane and methanol (19:1, V/V)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-c6c936c6f99a4e65b60e6e3bd147ac6e
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

Loading…