Hydrochloric Acid → (2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 1182269Notes

Reaction equation

HRID 1182269 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>[OH-].[Na+]>[C:9]1([S:15]([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 145742L-Proline

Product 1

HCID 720844(2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of d/l-proline (2.0 g, 6.8 mmol) in aqueous sodium hydroxide (1M, 34.7 mL) chilled at 0° C., was added phenylsulfonyl chloride (2.21 mL, 17.0 mmol) slowly. The reaction was stirred overnight at room temperature. The reaction mixture was acidified with HCl (20 ml, aqueous, 1 N) and extracted with diethyl ether (2×20 mL). The combined organic extracts were then dried over magnesium sulfate and concentrated under reduced pressure to give the desired N-phenylsulfonyl proline (1.7 g) as a white solid used without any further purification.

Workup

  1. extractionextracted with diethyl ether (2×20 mL)
  2. dry with materialThe combined organic extracts were then dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-535dd59dbcbb4036b8c0f9f593b0c43c
Source dataset
uspto-grants-2007_10
Patent number
US07288538B2

Reaction notes

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