Diethyl Ether → 1-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

HRID 891793Notes

Reaction equation

HRID 891793 reaction equation
[C:1]1(=[O:22])[N:5]([CH2:6][C:7]2[N:8]=[C:9]([N:12]3[CH2:15][CH:14]([OH:16])[CH2:13]3)[S:10][CH:11]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(N(CC)CC)C.C(OCC)C>C(Cl)Cl>[C:4]1(=[O:17])[N:5]([CH2:6][C:7]2[N:8]=[C:9]([N:12]3[CH2:13][CH:14]([O:16][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:15]3)[S:10][CH:11]=2)[C:1](=[O:22])[C:2]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:3]12

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222428071-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine

Product 1

HCID 222430451-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-phthalimidomethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (864 mg, 2.74 mmol) (obtained as described in Reference Example 68(2)) in methylene chloride (35 ml) were added methanesulfonyl chloride (0.25 ml, 3.29 mmol) and triethylamine (0.46 ml, 3.29 mmol) in an ice bath and the mixture was stirred for 1 hour. After checking the completion of the reaction, the mixture was added to diethyl ether and stirred for 30 minutes. The mixture was then filtered and the solid was collected by filtration and washed with diethyl ether to afford 1-(4-phthalimidomethyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (726 mg, yield 67%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. stirringstirred for 30 minutes
  3. filtrationThe mixture was then filtered
  4. filtrationthe solid was collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6d7559a2c11b4a7cbfc073b12530dae6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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