Hydrochloric Acid → [2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid

HRID 1592023Notes

Reaction equation

HRID 1592023 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:21])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:17][C:16](=[O:18])[NH:15][S:14]1(=[O:20])=[O:19].Cl>CO.O>[O:20]=[S:14]1(=[O:19])[NH:15][C:16](=[O:18])[CH2:17][N:13]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][C:5]([OH:21])=[O:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58997412[2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester2×

Product 1

HCID 58997414[2-(1,1,4-Trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2N aqueous NaOH (2.0 mL, 4.0 mmol) is added to a solution of the title compound of Example 40, [2-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid methyl ester (57 mg, 0.20 mmol) in MeOH (2.0 mL). The reaction is stirred for 3 h, then neutralized by addition of 2N aqueous HCl (2.0 mL). The mixture is concentrated on a Savant Speedvac to give a yellow solid. The solid is triturated with EtOAc, filtered and the filtrate is evaporated to give a yellow solid. This is dissolved in 2 mL water loaded onto a preparative reverse phase HPLC column (YMC CombiPrep Pro C18, 50×20 mm I.D., particle size S-5 micron, 12 nM) and eluted at 30 mL/min with a gradient of 90:10 (0.1% TFA in water:MeCN) to 10:90 over 5 min. Then held at 10:90 until 7 min. Fractions containing product are combined and concentrated on a Savant Speedvac to yield [2-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-acetic acid as a white solid: [M−1]−=269.

Workup

  1. concentrationThe mixture is concentrated on a Savant Speedvac
  2. customto give a yellow solid
  3. customThe solid is triturated with EtOAc
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. customto give a yellow solid
  7. washeluted at 30 mL/min with a gradient of 90:10 (0.1% TFA in water:MeCN) to 10:90 over 5 min
  8. waitThen held at 10:90 until 7 min
  9. additionFractions containing product
  10. concentrationconcentrated on a Savant Speedvac

Sources & evidence

ORD record
ord-aed5462d7f8f4177bff48965fa589182
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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