Triethylamine → HCID 178505329, compound

HRID 1170424Notes

Reaction equation

HRID 1170424 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([OH:15])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([O:15][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178525087HCID 178525087, compound

Product 1

HCID 178505329HCID 178505329, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cis-3-hydroxycyclobutane carboxylic benzyl ester (see WO03000657A1)(18.0 g, 87.5 mmol) in dichloromethane (155 m/L) was added triethylamine (18.3 mL, 131 mmol), and then thereto was added dropwise a solution of methanesulfonyl chloride (8.16 mL, 105 mmol) in dichloromethane (20 mL) at 0° C. for 15 minutes. The mixture was stirred for 1 hour, and then the reaction solution was washed with aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the titled compound (24.9 g, quant.).

Workup

  1. washthe reaction solution was washed with aqueous saturated sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-625941fd8cc747af821c0c4dae26a7c9
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

Loading…