Dichloromethane → 3-Isopropyl-4-(2-acetoxyethyl)-azetidinone

HRID 1719892Notes

Reaction equation

HRID 1719892 reaction equation
[CH:1]([C@H:4]1[C@H:7]([CH2:8][CH2:9][OH:10])[NH:6][C:5]1=[O:11])([CH3:3])[CH3:2].C(Cl)Cl.[C:15](Cl)(=[O:17])[CH3:16]>N1C=CC=CC=1>[CH:1]([CH:4]1[CH:7]([CH2:8][CH2:9][O:10][C:15](=[O:17])[CH3:16])[NH:6][C:5]1=[O:11])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 67926873Trans-3-isopropyl-4-(2-hydroxyethyl)-2-azetidinone

Product 1

HCID 199939093-Isopropyl-4-(2-acetoxyethyl)-azetidinone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trans-3-isopropyl-4-(2-hydroxyethyl)-2-azetidinone from Step B, is dissolved in 10 ml. CH2Cl2 and cooled to 0° C. Pyridine 0.75 ml is added and then 0.392 ml of acetyl chloride is added dropwise. The mixture is stirred at 0° for 15 min and then at 25° C. for another 15 minutes. The reaction mixture is evaporated to dryness. The residue is chromatographed on silica gel using 50% EtOAc/C6H6 as eluant to give 0.652 g 3-isopropyl-4-(2-acetoxyethyl)-azetidinone.

Workup

  1. waitat 25° C. for another 15 minutes
  2. customThe reaction mixture is evaporated to dryness
  3. customThe residue is chromatographed on silica gel using 50% EtOAc/C6H6 as eluant

Sources & evidence

ORD record
ord-fe8082f01ee044b29c4da929b49dc7bb
Source dataset
uspto-grants-1985_09
Patent number
US04543257

Reaction notes

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