Oxaprozin → beta-(4,5-Diphenyloxazol-2-yl)propionic acid calcium salt

HRID 358241

Reaction equation

HRID 358241 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].O.O.[Cl-].[Ca+2:27].[Cl-]>O.[OH-].[Na+]>[Ca+2:27].[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]([O-:22])=[O:21])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]([O-:22])=[O:21])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 4614OxaprozinHCID 5360545SodiumHCID 6093260Calcium chloride, dihydrate

Product 1

HCID 70488662beta-(4,5-Diphenyloxazol-2-yl)propionic acid calcium salt

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

β-(4,5-Diphenyloxazol-2-yl)propionic acid (oxaprozin) was converted to the sodium salt by stirring the acid (6 kg) in distilled water (60 kg) and 46-48% sodium hydroxide liquor (1.85 kg). A filtered solution of calcium chloride dihydrate B.P. (2.44 kg) in distilled water was added and the title compound precipitated as a white solid. This was collected on a vacuum filter and washed with distilled water until the filtrate was free from chloride. The product was dried in an air oven to give a yield of 6.7 kg (98% of theory) of the title compound as a tetrahydrate.

Workup

  1. customthe title compound precipitated as a white solid
  2. customThis was collected on a vacuum
  3. filtrationfilter
  4. washwashed with distilled water until the filtrate
  5. customThe product was dried in an air oven

Sources & evidence

ORD record
ord-4189c16cdb4e4027b1c300b2c1f8dc83
Source dataset
uspto-grants-1984_08
Patent number
US04465838

Linked notes

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