Acetic Acid → HCID 22242991, compound

HRID 891626Notes

Reaction equation

HRID 891626 reaction equation
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](OCC)=[O:29])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:33]([O:50][CH2:51][CH2:52][NH2:53])([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C[Al](C)C.C(O)(=O)C.C(OCC)(=O)C>C1C=CC=CC=1>[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:29])[NH:53][CH2:52][CH2:51][O:50][Si:33]([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:27]=2)[CH2:20]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl Acetate2×HCID 22242904HCID 22242904, compoundHCID 222429823-t-Butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine

Product 1

HCID 22242991HCID 22242991, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Subsequently, to a solution of 3-t-butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)azetidine (1.16 g, 2.49 mmol) (obtained as described in Reference Example 2(1)) in benzene (8.5 ml) was added a solution of 0.67M 2-(t-butyldiphenylsilyloxy)ethylamine-trimethylaluminium in benzene (6.42 ml) at room temperature under an atmosphere of nitrogen. The mixture was heated under reflux for 5 hours. After checking the completion of the reaction, 10% aqueous acetic acid solution (50 ml) and ethyl acetate (200 ml) were added to the reaction mixture, and the resulting mixture was stirred at room temperature for 1 hour. After adding ethyl acetate thereto, the reaction mixture was partitioned between ethyl acetate and water. 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 hexane:ethyl acetate (3:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-{4-[2-(t-butyldiphenylsilyloxy)ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.68 g, yield 94%) as a pale brown solid.

Workup

  1. customat room temperature
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. additionwere added to the reaction mixture
  5. customthe reaction mixture was partitioned between ethyl acetate and water
  6. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f64bfe91c6f34462a77380ed0cc06458
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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