Triethylamine → HCID 86754827, compound

HRID 1603653Notes

Reaction equation

HRID 1603653 reaction equation
C([S:4][C@H:5]1[N:8]([CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:22])[C@@H:6]1[Br:23])(=O)C.[N+]([O-])([O-])=O.[Ag+:28].C(N(CC)CC)C>CO>[Br:23][C@@H:6]1[C@@H:5]([S-:4])[N:8]([CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[O:11])[C:7]1=[O:22].[Ag+:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24470Silver NitrateHCID 54485418HCID 54485418, compound

Product 1

HCID 86754827HCID 86754827, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of p-methoxybenzyl [(3S, 4R)-4-acetylthio-3-bromo-2-oxoazetidin-1-yl]acetate (4.13 g, 0.01 mol) in methanol (90 ml) was added with stirring in subdued light to a solution of silver nitrate (2.27 g, 0.0133 mol) in methanol (90 ml). Triethylamine (1.87 ml, 0.0133 mol) was then added with ice cooling, and stirring continued for 1 hr. at 5-10° C. followed by 30 min. at room temperature. The mixture was re-cooled (ice bath) and the precipitated solid filtered and washed twice with ice cold methanol then hexane to give the title compound, yield, 4.6 g (96%).

Workup

  1. waitat 5-10° C. followed by 30 min. at room temperature
  2. temperatureThe mixture was re-cooled (ice bath)
  3. filtrationthe precipitated solid filtered
  4. washwashed twice with ice cold methanol

Sources & evidence

ORD record
ord-6029affae12e454fa9e3ad68d0b05a5a
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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