Water → N-[4-methoxybenzenesulfonyl]-(D)-asparagine

HRID 2209709

Reaction equation

[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].O.C(N(CC)CC)C.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>O1CCOCC1>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:28])=[O:27])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

D-asparagine (13.2 g, 100.0 mmol) is dissolved in dioxane 1,75.0 mL) and water (125.0 mL), triethylamine (21.0 mL, 150.0 mmol) is added, and the solution is cooled to 0° C. To this solution is added 4-methoxybenzenesulfonyl chloride (22.7 g, 110.0 mmol) over 10 minutes. The reaction is warmed to room temperature and stirred for 3 days. The precipitate is then filtered off, the filtrate is acidified to pH=~4, and extracted well with ethyl acetate. A first crop of pure product precipitates from the ethyl acetate and is collected by filtration. A second crop is obtained by evaporating off the ethyl acetate, and rinsing the solid obtained with water to remove inorganic salts. The two crops are combined to give N-[4-methoxybenzenesulfonyl]-(D)-asparagine.

Workup

temperatureThe reaction is warmed to room temperature
filtrationThe precipitate is then filtered off
extractionextracted well with ethyl acetate
customA first crop of pure product precipitates from the ethyl acetate
filtrationis collected by filtration
customA second crop is obtained
customby evaporating off the ethyl acetate
washrinsing the solid
customobtained with water
customto remove inorganic salts

Sources & evidence

ORD record: ord-186a678734c54e59bc312368c8900fe1
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455258

Linked notes

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