Triethylamine → HCID 22242929, compound

HRID 891748Notes

Reaction equation

HRID 891748 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([C:11]([N:13]3[CH2:16][CH:15]([NH:17][C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=4)=[O:19])[CH2:14]3)=[O:12])[N:10]=2)[CH2:3]1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>C(Cl)Cl.N1C=CC=CC=1>[CH3:31][S:32]([O:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([C:11]([N:13]3[CH2:14][CH:15]([NH:17][C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=4)=[O:19])[CH2:16]3)=[O:12])[N:10]=2)[CH2:3]1)(=[O:34])=[O:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22242799HCID 22242799, compound

Product 1

HCID 22242929HCID 22242929, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (630 mg, 1.45 mmol) (obtained as described in Reference Example 57(5)) in a mixture of methylene chloride (32 ml) and pyridine (12 ml) were added methanesulfonyl chloride (377 μl, 4.36 mmol) and triethylamine (611 μl, 4.36 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 4 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. To the residue were added ethyl acetate and diisopropyl ether, and the mixture was filtered off and washed with diisopropyl ether to afford 3-methanesulfonyloxy-1-{4-[3-(p-nitrobenzyloxycarbonylamino)-azetidine-1-carbonyl]-1,3-thiazol-2-yl}azetidine (766 mg, yield 100%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride 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. additionTo the residue were added ethyl acetate and diisopropyl ether
  8. filtrationthe mixture was filtered off
  9. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-3ab1fc484cf5476fba3c109ade3e9d7a
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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