Sodium Hydroxide → HCID 58997406, compound

HRID 1592016Notes

Reaction equation

HRID 1592016 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]2[CH2:16][C:15](=[O:17])[NH:14][S:13]2(=[O:19])=[O:18])[CH:7]=1>O.CO>[O:19]=[S:13]1(=[O:18])[NH:14][C:15](=[O:17])[CH2:16][N:12]1[C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[C:5]([OH:20])=[O:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9993263HCID 9993263, compound

Product 1

HCID 58997406HCID 58997406, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (105.4 mg, 2.64 mmol) in water (2.54 g) is added to a solution of the Example 37 title compound, 3-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-benzoic acid methyl ester (37.1 mg, 0.137 mmol) in MeOH (5.48 mL). This is allowed to stir 13 h and then neutralized by addition of 1N aqueous HCl (2.64 mL). The reaction mixture is loaded onto a preparative reverse phase HPLC column (YMC CombiPrep Pro C18, 50×20 mm I.D., particle size S-5 micron, 12 nM) in two equal aliquots and eluted at 30 mL/min with a gradient of 100:0 (water containing 0.1% TFA: MeCN) for 0 min to 2.5 min, then to 10:90 at 5.5 min. Then held at 10:90 until 7 min. Fractions containing the product are combined and concentrated on a Savant Speedvac to yield 3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzoic acid as a white powder: API-Ms [M−H]=255.09.

Sources & evidence

ORD record
ord-beac9920c864474c91251bced93713f7
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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