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

HRID 1702570Notes

Reaction equation

HRID 1702570 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 washing 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. washwashing with water
  4. customdrying
  5. customevaporating

Sources & evidence

ORD record
ord-458b6c45563b48858cb2f6ef13e5498d
Source dataset
uspto-grants-1982_09
Patent number
US04348320

Reaction notes

Loading…