Benzenesulfonyl chloride → 3-t-Butyldiphenylsilyloxy-1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]azetidine

HRID 891779Notes

Reaction equation

HRID 891779 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]([N:10]2[CH2:13][CH:12]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11]2)[S:8][CH:9]=1)=[N+]=[N-].[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C>CO.[OH-].[Pd+2].[OH-]>[Si:15]([O:14][CH:12]1[CH2:13][N:10]([C:7]2[S:8][CH:9]=[C:5]([CH2:4][NH:1][S:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:40])=[O:39])[N:6]=2)[CH2:11]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 222427481-(4-Azidomethyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine

Product 1

HCID 222428633-t-Butyldiphenylsilyloxy-1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]azetidineYield 28.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1-(4-Azidomethyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine (2.12 g, 4.71 mmol) (obtained as described in Reference Example 62(1)) in methanol (106 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide (2.12 g) at room temperature. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst and the filtrate concentrated under reduced pressure. The residue was dissolved in methylene chloride (100 ml). To the mixture were added benzenesulfonyl chloride (0.90 g, 7.07 mmol) and triethylamine (0.98 ml, 7.07 mmol) in an ice bath, and the mixture was stirred at room temperature for 2 hours. After checking the completion of the reaction, the mixture was distilled under reduced pressure. The residue 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 3-t-butyldiphenylsilyloxy-1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]azetidine (755 mg, yield 28%) as pale yellow oil.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered in order
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride (100 ml)
  6. customthe completion of the reaction
  7. distillationthe mixture was distilled under reduced pressure
  8. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  9. washThe organic layer was washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-49363f8e03d84af19f8dea37b7236858
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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