Pyridine → HCID 13491727, compound

HRID 345238Notes

Reaction equation

HRID 345238 reaction equation
[CH2:1]([O:8][C:9]([CH:11](O)[N:12]1[CH:15]([CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:32])=O>C1COCC1>[CH2:1]([O:8][C:9]([CH:11]([Cl:32])[N:12]1[CH:15]([CH2:16][CH2:17][O:18][C:19](=[O:21])[CH3:20])[CH2:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 13491726HCID 13491726, compound

Product 1

HCID 13491727HCID 13491727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

1-(Benzyloxycarbonyl hydroxymethyl)-4-(2-acetoxyethyl)-2-azetidinone (1.8 g) is dissolved in 30 ml THF under N2 and cooled to -20° C. Pyridine 0.45 ml is added and then thionylchloride (0.390 ml in 4 ml THF) is added dropwise over 2 minutes. The reaction mixture is stirred at -20° C., for 5 minutes. The cooling bath is removed and the reaction mixture is stirred for another 25 minutes. The reaction mixture is diluted with 30 ml benzene and filtered. The filtrate is evaporated under reduced pressure at 5° C. The residue is 1-(benzyloxycarbonylchloromethyl)-4-(2-acetoxyethyl)-2-azetidinone which is used directly in the next reaction.

Workup

  1. customThe cooling bath is removed
  2. stirringthe reaction mixture is stirred for another 25 minutes
  3. additionThe reaction mixture is diluted with 30 ml benzene
  4. filtrationfiltered
  5. customThe filtrate is evaporated under reduced pressure at 5° C
  6. customis used directly in the next reaction

Sources & evidence

ORD record
ord-f5cc14bb46e842e9a82fd08892f21f8f
Source dataset
uspto-grants-1991_10
Patent number
US05055573

Reaction notes

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