Hydrochloric Acid → HCID 56629638, compound

HRID 1788678Notes

Reaction equation

HRID 1788678 reaction equation
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[C@H:3]([CH3:5])[OH:4].[OH-].[Na+].Cl.[CH3:12][S:13]([N:16]1[CH2:20][CH2:19][N:18]([C:21](Cl)=[O:22])[C:17]1=[O:24])(=[O:15])=[O:14]>O.CC(C)=O>[OH:4][C@@H:3]([CH3:5])[C@@H:2]([NH:1][C:21]([N:18]1[CH2:19][CH2:20][N:16]([S:13]([CH3:12])(=[O:15])=[O:14])[C:17]1=[O:24])=[O:22])[C:6]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 69435D-ThreonineHCID 30162993-(Methylsulphonyl)-2-oxoimidazolidine-1-carbonyl chloride

Product 1

HCID 56629638HCID 56629638, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

D-Threonine (5.0 g) was suspended in water (50 ml) and treated with 2M aqueous sodium hydroxide solution to pH 10, forming a clear solution. The pH was then re-adjusted to 7.5 with concentrated hydrochloric acid and the still clear solution cooled to 15°. 3-Methanesulphonyl-2-oxoimidazolidine-1-carbonyl chloride (9.5 g) was then added portionwise over 2 minutes, with simultaneous addition of 2M aqueous sodium hydroxide to maintain the pH at 6.0-7.5. Following this, acetone (30 ml) was added to give a clear solution which was then stirred at room temperature for 1 hour whilst still maintaining the pH at 6.0-7.5. After evaporation of the acetone in vacuo the aqueous residue was extracted well with ethyl acetate and the organic extracts were discarded. The pH of the aqueous phase was then adjusted to 1.5 with concentrated hydrochloric acid and the mixture was extracted using 3×50 ml portions of ethyl acetate:tetrahydrofuran (1:1). The organic extracts were dried and the solvent was evaporated to give the title compound as a white solid, (7.3 g).

Workup

  1. customforming a clear solution
  2. temperatureto maintain the pH at 6.0-7.5
  3. additionwas added
  4. customto give a clear solution which
  5. temperaturestill maintaining the pH at 6.0-7.5
  6. customAfter evaporation of the acetone in vacuo the aqueous residue
  7. extractionwas extracted well with ethyl acetate
  8. extractionthe mixture was extracted
  9. customThe organic extracts were dried
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cdb7f170466e44ea945ffad42c2724c9
Source dataset
uspto-grants-1987_08
Patent number
US04684641

Reaction notes

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