Water → HCID 49805873, compound

HRID 1615067Notes

Reaction equation

HRID 1615067 reaction equation
Cl.[NH:2]1[CH2:6][C@@H:5]([OH:7])[C@H:4]([OH:8])[CH2:3]1.O.C([O-])([O-])=O.[Na+].[Na+].CS(O[CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([N:32]2[CH2:35][CH:34]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][C:47]([CH2:50][CH3:51])=[CH:46][CH:45]=4)=[C:38]([O:52][CH3:53])[CH:37]=3)[CH2:33]2)=[O:31])[CH:25]=1)(=O)=O>C(O)CC>[OH:8][C@H:4]1[C@H:5]([OH:7])[CH2:6][N:2]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]([N:32]3[CH2:33][CH:34]([C:36]4[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]5[CH:45]=[CH:46][C:47]([CH2:50][CH3:51])=[CH:48][CH:49]=5)=[C:38]([O:52][CH3:53])[CH:37]=4)[CH2:35]3)=[O:31])[CH:25]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 57463459(3R,4R)-Pyrrolidine-3,4-diolHCID 59633892HCID 59633892, compound2×

Product 1

HCID 49805873HCID 49805873, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixed solution of (3R,4R)-pyrrolidine-3,4-diol monohydrochloride (2.1 g) in 1-propanol (60 mL)/water (2.0 mL) was added Na2CO3 (4.0 g). The mixture was stirred at 60° C. for 1 hr. To the mixture was added 2-(2-{3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidine-1-carbonyl}pyridin-4-yloxy)ethyl methanesulfonate (6.7 g) prepared in (1). The reaction mixture was stirred at 100° C. for 10 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=40/1 to 5/1) to give the title compound (4.7 g, 70%).

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 10 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=40/1 to 5/1)

Sources & evidence

ORD record
ord-23469b1cc12b4289b091d6eece84db2a
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

Loading…