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Ethanol → 3-t-Butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine

HRID 891546
Notes
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Reaction equation

HRID 891546 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:14][CH:13]([OH:15])[CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[Si:16](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CN=C1.C(O)C>CN(C)C=O>[Si:16]([O:15][CH:13]1[CH2:12][N:11]([C:8]2[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=2)[CH2:14]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 22242978Ethyl 2-(3-hydroxyazetidin-1-yl)-1,3-thiazole-4-carboxylate

Product 1

HCID 222429823-t-Butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidineYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (8.5 g, 37.2 mmol) (obtained as described in Reference Example 1(2)) in dimethylformamide (255 ml) were added t-butyldiphenylsilyl chloride (19.4 ml, 74.5 mmol) and imidazole (5.07 g, 74.5 mmol) in an ice bath. After stirring the mixture in an ice bath for 10 minutes, the resulting mixture was stirred at room temperature for 2.5 hours. After checking the completion of the reaction, ethanol (2.59 ml) was added to the reaction mixture in an ice bath and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and 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 n-hexane:ethyl acetate (6:1→2:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine (14.85 g, yield 86%) as a pale brown solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2.5 hours
  2. additionwas added to the reaction mixture in an ice bath
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. customThe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-caee715f99a241bba69de3d94ba7cf91
Source dataset
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07001897B2

Reaction notes

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