Hydrogen Bromide → HCID 22814996, compound

HRID 1632349Notes

Reaction equation

HRID 1632349 reaction equation
Cl[C:2]1[CH2:6][C@@H:5]([C@H:7]([N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[C:8]([O:10]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:9])[O:4][N:3]=1.[BrH:35]>[N+](C)([O-])=O>[Br:35][C:2]1[CH2:6][C@@H:5]([C@H:7]([N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[C:8]([OH:10])=[O:9])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12939897HCID 12939897, compound

Product 1

HCID 22814996HCID 22814996, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To 185 mg (0.4 mmole) of the (αS,5S)-chloro-4,5-dihydro-α-phthalimido-5-isoxazole acetic acid, benzhydryl ester in 3 ml of dry nitromethane in an ice bath under nitrogen is bubbled dry hydrogen bromide for five minutes. The bath is removed and the solution stirred for one hour. After concentrating the solution is vacuo the residue is chromatographed on CC-4 silica gel (30 g) with 30%) ethyl concentrating the solution in vacuo the residue is chromatographed on CC-4 silica gel (30 g) with 30%) ethyl acetate/hexane to yield 115 mg of a white foam. This foam is recrystallized from 4/1 hexane/ethanol to yield 3-bromo-4,5-dihydro-α-phthalimido-5-isoxazole acetic acid.

Workup

  1. customThe bath is removed
  2. concentrationAfter concentrating the solution
  3. customis chromatographed on CC-4 silica gel (30 g) with 30%) ethyl concentrating the solution in vacuo the residue
  4. customis chromatographed on CC-4 silica gel (30 g) with 30%) ethyl acetate/hexane

Sources & evidence

ORD record
ord-2ba29df665594d27955130a2588d8c3e
Source dataset
uspto-grants-1984_10
Patent number
US04474968

Reaction notes

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