Pyridine → HCID 22812919, compound

HRID 224550Notes

Reaction equation

HRID 224550 reaction equation
[CH2:1]([O:5][C@H:6]1[N:9]([CH:10](O)[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:28])[C@@H:7]1[NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]([CH3:4])=[O:3].S(Cl)([Cl:41])=O.N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([O:5][C@H:6]1[N:9]([CH:10]([Cl:41])[C:11]([O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:8](=[O:28])[C@@H:7]1[NH:29][C:30](=[O:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 22812922HCID 22812922, compound

Product 1

HCID 22812919HCID 22812919, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diphenylmethyl α-[4(R)-acetonyloxy-3(R)-phenylacetamido-2-oxo-azetidin-1-yl]glycolate (2.136 g) in anhydrous methylene chloride (20 ml) are added thionyl chloride (0.90 ml) and pyridine (0.33 ml) with stirring at 0° C. After stirring for 1 hour at 0° C., the mixture is poured into ice water, and extracted with ethyl acetate. The organic layer is washed with water, dried over sodium sulfate, and evaporated under reduced pressure to give the crude product of a mixture of epimers at position α.

Workup

  1. stirringAfter stirring for 1 hour at 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give

Sources & evidence

ORD record
ord-cac1d3303a4c42aa9299ffbecee3121a
Source dataset
uspto-grants-1980_11
Patent number
US04233216

Reaction notes

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