Sodium Hydroxide → HCID 178524666, compound

HRID 2215860Notes

Reaction equation

HRID 2215860 reaction equation
[NH:1]1[CH2:3][C@H:2]1[C:4]([OH:6])=[O:5].[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](Cl)(=[O:18])=[O:17])([O-:9])=[O:8].[OH-].[Na+]>CC(C)=O>[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([N@:1]1[CH2:3][CH:2]1[C:4]([OH:6])=[O:5])(=[O:18])=[O:17])([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 155402-Nitrobenzenesulfonyl chlorideHCID 11286438(2S)-2-Aziridinecarboxylic acid

Product 1

HCID 178524666HCID 178524666, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2 °C

Procedure

The liquid reaction mixture containing 9.21 g (106 mmol) of (S)-aziridine-2-carboxylic acid obtained in Example 1 was cooled to 2° C. and 150 mL of acetone was added thereto at an internal temperature of 2 to 5° C. While maintaining this solution at an internal temperature of −6 to −2° C., a mixture of 26.9 g (121 mmol) of 2-nitrobenzenesulfonyl chloride with 50 mL of acetone was added thereto over 1 hour. Then the reaction was continued as such for additional 2 hours. During the reaction, a 30 wt. % aqueous solution of sodium hydroxide was added to maintain the reaction system at pH 10.0 to 10.5 The obtained liquid reaction mixture contained 26.9 g (99 mmol) of (S)-N-2-nitrobenzenesulfonyl-aziridine-2-carboxylic acid (yield: 93%).

Workup

  1. customThe liquid reaction mixture
  2. customat an internal temperature of 2 to 5° C
  3. temperatureWhile maintaining this solution at an internal temperature of −6 to −2° C.
  4. additionwas added
  5. customsuch for additional 2 hours
  6. customDuring the reaction
  7. temperatureto maintain the reaction system

Sources & evidence

ORD record
ord-23ae275ab5a443a3aa6435d46c860797
Source dataset
uspto-grants-2006_09
Patent number
US07109352B2

Reaction notes

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