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Triethylamine → 3-t-Butyldiphenylsilyloxy-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine

HRID 891787
Notes
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Reaction equation

HRID 891787 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-].[O:32]1[CH:36]=[CH:35][CH:34]=[C:33]1[C:37](Cl)=[O:38].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][C:37]([C:33]3[O:32][CH:36]=[CH:35][CH:34]=3)=[O:38])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 222427481-(4-Azidomethyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine

Product 1

HCID 222429493-t-Butyldiphenylsilyloxy-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidineYield 60%

Reagents, catalysts & solvents 2

HCID 9942167
Palladium hydroxide
Catalyst
HCID 887MethanolSolvent

Procedure

1-(4-Azidomethyl-1,3-thiazol-2-yl)-3-t-butyldiphenylsilyloxyazetidine (2.47 g, 5.50 mmol) (obtained as described in Reference Example 62(1)) in methanol (120 ml) was subjected to catalytic reduction in the presence of 20% palladium hydroxide (2.47 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 (115 ml). To the mixture were added 2-furoyl chloride (0.65 ml, 6.60 mmol) and triethylamine (0.92 ml, 6.60 mmol), and the mixture was stirred at room temperature for 1 hour. 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 hexane:ethyl acetate (1:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine (1.60 g, yield 60%) as a 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 (115 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-25a71f152b484ee08111173a62b4f872
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07001897B2

Reaction notes

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