Acetic Acid → HCID 22243005, compound

HRID 891595Notes

Reaction equation

HRID 891595 reaction equation
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28](OCC)=O)[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.C[NH2:34].C[Al](C)C.C(O)(=O)C>C1C=CC=CC=1>[Si:1]([O:18][CH:19]1[CH2:20][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]#[N:34])[N:27]=2)[CH2:22]1)([C:14]([CH3:16])([CH3:17])[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

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 22242773HCID 22242773, compoundHCID 22243059HCID 22243059, compound

Product 1

HCID 22243005HCID 22243005, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-ethoxycarbonyl-1,3-oxazol-2-yl)azetidine (357 g, 0.79 mmol) (obtained as described in Reference Example 21(3)) in benzene (8 ml) was added a solution of 0.67M methylamine-trimethylaluminium in benzene (2.8 ml) at room temperature under an atmosphere of nitrogen. The mixture was stirred in a water bath (60° C.) for 7 hours. After checking the completion of the reaction, 10% aqueous acetic acid solution (10 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 water. The obtained organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using hexane:ethyl acetate (5:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-cyano-1,3-oxazol-2-yl)azetidine (130 mg, yield 41%) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-33be88a80cc847bf8f345d2bcb666cd3
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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