Hydrochloric Acid → HCID 89534494, compound

HRID 1528205Notes

Reaction equation

HRID 1528205 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Na+].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29].Cl>O.C(OCC)(=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[C:7]([O:9][CH3:10])=[O:8])(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 10340Sodium CarbonateHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 89534494HCID 89534494, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., a solution of 0.647 g (3.9 mmol) of methyl (S)-pyrrolidine-2-carboxylate hydrochloride in 6 ml of water was added to 0.83 g of sodium carbonate (7.8 mmol, 2 eq), followed portionwise by 1.0 g (3.9 mmol) of 4-chloro-3-nitrobenzenesulfonyl chloride. The medium was stirred at 0° C. for 4 hours. The reaction medium was diluted with ethyl acetate and brought to pH 5-6 with 2 N HCl. After extraction, the aqueous phase was basified with sodium bicarbonate and extracted twice with ethyl acetate. The organic phases were combined, washed with a saturated sodium chloride solution, dried over magnesium sulfate and evaporated. 1.22 g (90%) of product were obtained. Yield=90%.

Workup

  1. extractionAfter extraction
  2. extractionextracted twice with ethyl acetate
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-c1cfd8e56d6647f0a3035388e61798da
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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