2,6-Lutidine → HCID 56987241, compound

HRID 861895Notes

Reaction equation

HRID 861895 reaction equation
S(Cl)([Cl:3])=O.O[CH:6]([N:19]1[C@H:22]([CH2:23][CH2:24][C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][O:27]2)[C@H:21]([N:32]2[C:36](=[O:37])[C:35]3=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]3[C:33]2=[O:42])[C:20]1=[O:43])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:8].N1C(C)=CC=CC=1C>C1COCC1>[Cl:3][CH:6]([N:19]1[C@H:22]([CH2:23][CH2:24][C:25](=[O:31])[C@@H:26]2[CH2:30][CH2:29][CH2:28][O:27]2)[C@H:21]([N:32]2[C:36](=[O:37])[C:35]3=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]3[C:33]2=[O:42])[C:20]1=[O:43])[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24386Thionyl ChlorideHCID 53999217HCID 53999217, compound

Product 1

HCID 56987241HCID 56987241, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of thionyl chloride (530 μl, 7.27mmol) in THF (3 ml) was added to 4-methoxybenzyl (RS)-2-hydroxy-2-[(3S, 4R)-4-[3-oxo-3-[(S)-tetrahydrofuran-2-yl]propyl]-3-phthalimidoazetidin-2-on-1-yl]acetate (2.59 g, 4.84 mmol) and 2,6-lutidine (850 μl, 7.30 mmol) in THF (50 ml) at -20° C. After stirring for 1 h, the reaction mixture was filtered through a pad of celite, and the filtrate evaporated in vacuo. Toluene was added and re-evaporated to yield 4-methoxybenzyl (RS)-2-chloro-2-[(3S,4R)-4-[3-oxo-3-[(S)-tetrahydrofuran-2-yl]propyl]-3-phthalimidoazetidin-2-on-1-yl]acetate.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. customthe filtrate evaporated in vacuo
  3. additionToluene was added
  4. customre-evaporated

Sources & evidence

ORD record
ord-e660fe736afc4dfc9b1c59886adf5c41
Source dataset
uspto-grants-1998_02
Patent number
US05716948

Reaction notes

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