3-Bromo-4-oxo-4-phenylbutanoic acid → HCID 86739401, compound

HRID 543884Notes

Reaction equation

HRID 543884 reaction equation
[C:1]([CH:9]([Br:14])[CH2:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][N:16]1[CH2:21][N:20]([CH3:22])[CH2:19][NH:18][C:17]1=[S:23]>CO>[CH:1]([O-:8])([CH3:9])[CH3:2].[Br-:14].[C:11]([CH2:10][CH:9]1[S:23][C:17]2=[N+:16]([CH3:15])[CH2:21][N:20]([CH3:22])[CH2:19][N:18]2[C:1]1([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:13])=[O:12].[C:11]([CH2:10][CH:9]1[S:23][C:17]2=[N+:16]([CH3:15])[CH2:21][N:20]([CH3:22])[CH2:19][N:18]2[C:1]1([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:8])([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 2562953-Bromo-4-oxo-4-phenylbutanoic acidHCID 204611451,5-Dimethyl-1,3,5-triazinane-2-thione

Product 1

HCID 86739401HCID 86739401, compoundYield 153.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-benzoyl-3-bromo propionic acid (6.4 g, 0.025 moles) in methanol (40 ml) was mixed with a solution of 1,5-dimethyl-3,4,5,6-tetrahydro-s-triazin-2(1H)thione (3.625 g, 0.025 mole) in the same solvent (100 ml). After 2 hours at room temperature the solvent was evaporated to give a foam which was crystallised from isopropanol to give 7-carboxymethyl-1,3-dimethyl-6-hydroxy-6-phenyl-3,4,5,7-tetrahydro-2H-thiazolo[3,2-a]-s-triazinium bromide isopropanolate (10.05 g,), m.p. 154°-155° C. (decomposition).

Workup

  1. customAfter 2 hours at room temperature the solvent was evaporated
  2. customto give a foam which
  3. customwas crystallised from isopropanol

Sources & evidence

ORD record
ord-435f5cc3d7424baa960352064bbc3721
Source dataset
uspto-grants-1984_05
Patent number
US04447604

Reaction notes

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