Hydrochloric Acid → HCID 178524666, compound

HRID 2085564Notes

Reaction equation

HRID 2085564 reaction equation
Cl[CH2:2][C@H:3]([C:5]([OH:7])=[O:6])[NH2:4].O.[OH-].[Li+].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21])([O-:13])=[O:12].Cl>O.C(OCC)(=O)C.CC(C)=O>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([N@:4]1[CH2:2][CH:3]1[C:5]([OH:7])=[O:6])(=[O:22])=[O:21])([O-:13])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 155402-Nitrobenzenesulfonyl chlorideHCID 168937Lithium hydroxide, monohydrate2×HCID 439771(2S)-2-amino-3-chloropropanoic acid

Product 1

HCID 178524666HCID 178524666, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

200 mg (1.62 mmol) of (S)-3-chloroalanine was dissolved in 4.0 mL of water. After adding 136 mg (3.24 mmol) of lithium hydroxide monohydrate, the resulting mixture was slowly heated to 50° C. and then stirred for 3 hours. The reaction container was ice-cooled and 6.4 mL of acetone, 431 mg (1.94 mmol) of 2-nitrobenzenesulfonyl chloride and 68 mg (1.62 mmol) of lithium hydroxide monohydrate were successively added thereto at an internal temperature of 5° C. After 1 hour, 30 mL of ethyl acetate was added. Further, 6 N hydrochloric acid was added to adjust to pH 2.0. Then the reaction mixture was divided into layers and the organic layer was collected. The aqueous layer was extracted with 50 mL portions of ethyl acetate twice to give an organic layer. The organic layers thus obtained were combined, washed successively with 50 mL of water and 50 mL of a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and filtered. After distilling off the solvent under reduced pressure, 265 mg of (S)-N-2-nitrobenzenesulfonyl-aziridine-2-carboxylic acid was obtained. Yield: 60%.

Workup

  1. temperaturecooled
  2. customat an internal temperature of 5° C
  3. waitAfter 1 hour
  4. customthe organic layer was collected
  5. extractionThe aqueous layer was extracted with 50 mL portions of ethyl acetate twice
  6. customto give an organic layer
  7. customThe organic layers thus obtained
  8. washwashed successively with 50 mL of water and 50 mL of a saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-3732b677021d496c979ec22ec5fc9134
Source dataset
uspto-grants-2004_04
Patent number
US06720449B2

Reaction notes

Loading…