Sodium Hydroxide → HCID 14182673, compound

HRID 1788652Notes

Reaction equation

HRID 1788652 reaction equation
[NH2:1][CH:2]([C:6]1[N:7]=[CH:8][S:9][CH:10]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[O:13]=[C:14]1[N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:17][CH2:16][N:15]1[C:23](Cl)=[O:24]>O>[O:13]=[C:14]1[N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:17][CH2:16][N:15]1[C:23]([NH:1][CH:2]([C:6]1[N:7]=[CH:8][S:9][CH:10]=1)[C:3]([OH:5])=[O:4])=[O:24]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 30162993-(Methylsulphonyl)-2-oxoimidazolidine-1-carbonyl chlorideHCID 14182672HCID 14182672, compound

Product 1

HCID 14182673HCID 14182673, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DL-2-Amino-2-(thiazol-4-yl)acetic acid (214 mg) [prepared by the method described in J. Med. Chem. 16, 978 (1973)] was taken up in water (10 ml) and the pH was adjusted to 6.5 by the addition of 2N sodium hydroxide solution. 2-Oxo-3-methylsulphonylimidazolidin-1-ylcarbonyl chloride (310 mg) was added to the stirred solution at room temperature in portions; the pH being maintained between 6.0 and 7.0 by the addition of 2N sodium hydroxide solution. When the addition was complete, the mixture was stirred for one hour, filtered, and the filtrate was washed with ethyl acetate (2×20 ml), acidified to pH 1.0, and extracted with ethyl acetate (2×20 ml). The combined extracts were washed with saturated sodium chloride solution (20 ml), dried (MgSO4), filtered and evaporated to dryness in vacuo. The residue was triturated with methylene chloride and the solid product was separated by filtration to give the title compound as a white solid, (250 mg).

Workup

  1. additionWhen the addition
  2. filtrationfiltered
  3. washthe filtrate was washed with ethyl acetate (2×20 ml)
  4. extractionextracted with ethyl acetate (2×20 ml)
  5. washThe combined extracts were washed with saturated sodium chloride solution (20 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customThe residue was triturated with methylene chloride
  10. customthe solid product was separated by filtration

Sources & evidence

ORD record
ord-4c4b391c193843ba84207377c5f51841
Source dataset
uspto-grants-1987_08
Patent number
US04684642

Reaction notes

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