Pyridine → 1-(t-Butyldimethylsilyl)-4-(2-acetoxypropyl)-2-azetidinone

HRID 867580Notes

Reaction equation

HRID 867580 reaction equation
[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:15])[CH3:14])[CH2:10][C:9]1=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([O:15][C:23](=[O:25])[CH3:24])[CH3:14])[CH2:10][C:9]1=[O:16])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 143289891-(t-Butyldimethylsilyl)-4-(2-hydroxypropyl)-2-azetidinone

Product 1

HCID 143289901-(t-Butyldimethylsilyl)-4-(2-acetoxypropyl)-2-azetidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(t-butyldimethylsilyl)-4-(2-hydroxypropyl)-2-azetidinone (2.46 g) is dissolved in 20 ml CH2Cl2 cooled to 0° and treated with 0.90 g pyridine and 0.080 g of acetyl chloride (added dropwise). The reaction mixture is stirred at 0° for 15 min, allowed to warm to r.t. during the next 15 min and then worked up by dilution with CH2Cl2 and washed with water, drying and evaporating. The residue on chromatography on silica gel gives 1-(t-butyldimethylsilyl)-4-(2-acetoxypropyl)-2-azetidinone.

Workup

  1. temperaturecooled to 0°
  2. additionadded dropwise)
  3. washwashed with water
  4. customdrying
  5. customevaporating

Sources & evidence

ORD record
ord-211633928e474b46af630806cce56522
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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