Pyridine → p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 1680319Notes

Reaction equation

HRID 1680319 reaction equation
[C:1]([S:4][CH:5]1[N:8]([CH:9](O)[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:24])[CH2:6]1)(=[O:3])[CH3:2].N1C=CC=CC=1.O=S(Cl)[Cl:33]>O1CCCC1.O1CCOCC1>[C:1]([S:4][CH:5]1[N:8]([CH:9]([Cl:33])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 13132061HCID 13132061, compound

Product 1

HCID 13132062p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a cooled (0°) and stirred solution of p-nitrobenzyl 2-(4-acetylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate (3.79 g., 10.7 mmole) in tetrahydrofuran (40 ml.) and dioxane (40 ml.) was added pyridine (0.97 ml., 12 mmole) followed by SOCl2 (1.43 g., 0.88 ml., 12 mmole). The mixture was stirred 30 minutes at 0°, the precipitate was removed and washed with toluene, and the combined filtrates were concentrated on a rotary evaporator to leave a yellow oil. Partial purification was achieved by filtering the residue over a silica gel pad and washing with chloroform. δ(ppm, CDCl3): 8.2 (2H, m, aromatic), 7.55 (2H, m, aromatic), 6.12 (1H, s, CHCl), 5.65 (1H, m, H-4), 5.35 (2H, two s, benzylic H), 3.62 (1H, dd, J3-3 =16, J3-4 cis =6, H-3), 3.08 (1H, m, H-3), 2.35 (3H, two s, CH3). The product was obtained as a mixture of two epimers.

Workup

  1. temperatureTo a cooled (0°)
  2. customthe precipitate was removed
  3. washwashed with toluene
  4. concentrationthe combined filtrates were concentrated on a rotary evaporator
  5. customto leave a yellow oil
  6. customPartial purification
  7. filtrationby filtering the residue over a silica gel pad
  8. washwashing with chloroform
  9. customThe product was obtained as a mixture of two epimers

Sources & evidence

ORD record
ord-d1c7a522abf2464fad10bb9d410815aa
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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