Pyridine → HCID 22242986, compound

HRID 891777Notes

Reaction equation

HRID 891777 reaction equation
[C:1]([NH:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:19][CH:18]([OH:20])[CH2:17]2)[S:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl>[C:1]([NH:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:17][CH:18]([O:20][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:19]2)[S:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22243076HCID 22243076, compound

Product 1

HCID 22242986HCID 22242986, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[4-(benzoylaminomethyl)-1,3-thiazol-2-yl]-3-hydroxyazetidine (582 mg, 2.01 mmol) (obtained as described in Reference Example 64(2)) in methylene chloride (30 ml) were added methanesulfonyl chloride (0.19 ml, 2.41 mmol), triethylamine (0.34 ml, 2.41 mmol) and pyridine (5.8 ml) in an ice bath and the mixture was stirred for 1 hour. After checking the completion of the reaction, the 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 sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 1-[4-(benzoylaminomethyl)-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (739 mg, yield 100%) as a pale yellow solid.

Workup

  1. customthe completion of the reaction
  2. customthe 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 sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-3ccecfd2553740cb9fa64c334ce8c2f0
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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