Triethylamine → HCID 22242812, compound

HRID 891572Notes

Reaction equation

HRID 891572 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][O:9][C:10]([C:12]2[N:13]=[C:14]([N:17]3[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]3)[S:15][CH:16]=2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(CC)CC)C>C(Cl)Cl>[CH3:26][S:27]([O:23][CH:20]1[CH2:21][CH2:22][N:17]([C:14]2[S:15][CH:16]=[C:12]([C:10]([O:9][CH2:8][C:7]3[CH:24]=[CH:25][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[O:11])[N:13]=2)[CH2:18][CH2:19]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22243002HCID 22243002, compound

Product 1

HCID 22242812HCID 22242812, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (0.75 g, 2.06 mmol) (obtained as described in Reference Example 14(4)) in anhydrous methylene chloride (38 ml) were added methanesulfonyl chloride (0.18 ml, 2.33 mmol) and triethylamine (0.35 ml, 2.51 mmol) in an ice bath. The mixture was brought to room temperature in 10 minutes, and then stirred for 1 hour. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1) as the eluant to afford 4-methanesulfonyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (0.87 g, yield 96%) as a colorless solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-fb255152f324464b82d7b8cff7d31f8f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…